Category: 142808-15-9

Electric Literature of 142808-15-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Into a 50 mL dry, round bottom flask fitted with a magnetic stirring bar, a dropping funnel (25 mL) and a refluxing condenser was placed magnesium turnings (129 mg, 5.3 mmol) and anhydrous diethyl ether (4 mL). Anhydrous diethyl ether (16 mL) was added to the dropping funnel followed by 4-bromo- 2-fluoro-1-(trifluoromethyl)benzene (1.17 g, 4.8 mmol). A portion of the 4- bromo-2-fluoro-1-(trifluoromethyl)benzene solution (2 mL) as well as iodine (5 mg) was added to the flask which was then heated to reflux and stirred. Heating was stopped and the remainder of the 4-bromo-2-fluoro-1- (trifluoromethyl)benzene solution was added dropwise to the flask at such a rate that the solvent refluxed gently (about 10 minutes). After the addition was complete, the reaction was heated to reflux for 2 hours. The mixture was cooled to -78 C and a solution of 2-(2,6,6-trimethylcyclohex-1- enyl)acetaldehyde (200 mg, 1.2 mmol) in diethyl ether (3 mL) was added dropwise via syringe. The reaction was allowed to warm to room temperature and stirred for 4 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was diluted with water (20 mL) and the organics were extracted with diethyl ether (30 mL x 2). The combined organic phase was washed with brine (60 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleumether/ethyl acetate = 100/1 ) to afford the title compound as a yellow oil (138 mg, Yield: 35%). Rf = 0.6 (10:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCI3) delta 7.57 (t, J = 7.6 Hz, 1 H), 7.30-7.23 (m, 2H), 4.89 (t, J = 7.4 Hz, 1 H), 2.48-2.46 (m, 2H), 2.22 (d, J = 1 .2 Hz, 1 H), 2.12-1.96 (m, 2H), 1.68 (s, 3H), 1 .68-1 .62 (m, 2H), 1 .51 -1 .48 (m, 2H), 1 .07 (s, 3H), 1.06 (s, 3H) ppm; Mass spectrum (ESI +ve) m/z 331 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluorobenzotrifluoride, and friends who are interested can also refer to it.

Reference:
Patent; BIKAM PHARMACEUTICALS, INC.; QUACH, Tan; BERMAN, Judd; GARVEY, David, S.; WO2013/81642; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 142808-15-9, These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Place 4-bromo-2-fluorotrifluorotoluene (29.2 g, 120 mmol, 1 eq.) In a dropping funnel and set aside. Diisopropylamine (14.6g, 144mmol, 1.2eq.) And 220ml of tetrahydrofuran were added to the reaction flask, cooled to -78 C, and n-butyllithium (52.8ml, 132mmol, 1.1eq.) Was added dropwise under the protection of nitrogen. After the dropwise addition, the mixture was stirred at 25 C for 1 hour. Recool to -78 C and add 4-bromo-2-fluorotrifluorotoluene dropwise. After the dropwise addition, the mixture was stirred at -78 C for 2 hours. Iodomethane (18.7g, 132mmol, 1.1eq.) Was added dropwise, and the temperature was gradually raised to 25 C for 16 hours.[0058]After the reaction was completed, it was cooled in an ice water bath, and 150 ml of saturated ammonium chloride solution was added dropwise for quenching. It was extracted with ethyl acetate, and the organic phase was concentrated to obtain 26.8 g of yellow oily 1-bromo-3-fluoro-2-methyl-4- (trifluoromethyl) benzene in 87% yield. Used directly in the next step.

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; Ali Biological New Materials (Changzhou) Co., Ltd.; Shi Jianyun; Xu Yibo; Shi Hongliang; Dai Hongsheng; Zhang Jun; (6 pag.)CN110885290; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2-fluorobenzotrifluoride

0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl were added to 11 ml of toluene solution containing 1 g of the free form of the compound (F) obtained above and 0.73 g of 4-bromo-2-fluorobenzotrifluoride and the entire mixture was refluxed overnight under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the target compound. Viscous oil 1H-NMR(CDCl3, deltappm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q, 2H), 3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H), 7.16(d, 1H), 7.38(t, 1H)

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIPPON SODA CO., LTD.; HAMAMOTO, Isami; TAKAHASHI, Jun; YANO, Makio; KAWAGUCHI, Masahiro; HANAI, Daisuke; IWASA, Takao; EP1932844; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-fluorobenzotrifluoride

Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (5000 mL), NH(i-Pr)2 (249 g, 1.20 equiv). This was followed by the addition of n-BuLi (905 mL, 1.10 equiv) dropwise with stirring in 30 min at -70C. The resulting solution was stirred for 0.5 hr at -30C. To this was added 4-bromo-2-fluoro- l-(trifluoromethyl)benzene (500 g, 2.06 mol, 1.00 equiv) dropwise with stirring at -78C in 2 hr. The resulting solution was stirred for 2 hr at -78C. The reaction was then poured into 1000 g of C02(s) at -70C. The pH value of the solution was adjusted to 3 with hydrogen chloride (2N) (1.5 mol/L). The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 301 g (50%) of 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid as a white solid.

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 142808-15-9,Some common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, molecular formula is C7H3BrF4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation of 3-fluoro-4-trifluoromethylmagnesium bromide:Under nitrogen protection, add 24g of magnesium chips and 100mL of THF to a 2L four-necked flask, first add 3-fluoro-4-trifluoromethylbromobenzene 13g.The reaction was initiated at about 30 C. After the initiation, a solution of 230 g of 3-fluoro-4-trifluoromethylbromobenzene and 700 mL of THF was added dropwise at 40 C, and the mixture was dropped about 2 h.After the completion of the dropwise addition, the mixture was stirred at 50 C for 2 h, and the reaction was monitored by GC, and the raw material was converted to over 99.0%.Preparation of 2-amino-5-methyl-3′-fluoro-4′-trifluoromethyl-1,1′-biphenyl:Prepared 206 g of N-benzylidene-2-chloro-4-methylaniline and 10 g of anhydrous NiCl2 under nitrogen protection.Sphos 20g and THF 500mL were added to a 2L four-necked flask, and the prepared Grignard reagent was dropped into the reaction system at 50 C, and there was a significant exotherm. After the completion of the dropwise addition, the mixture was stirred for 3 hours.200 mL of 30% sulfuric acid was added and stirred at 50 C for 2 h.After removing THF under reduced pressure, the system was cooled to 0 C.Suction filtration to give a brown solid, the crude product is recrystallized from toluene and hepbrowne to give a slightly brown solid powder 215g, 99.0%, yield: 80.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-fluorobenzotrifluoride, its application will become more common.

Reference:
Patent; Shanghai Kangpeng Technology Co., Ltd.; Zeng Yuan; Zhou Yan; Li Bolan; Chen Xiaobin; Wang Daoxiang; Yang Jianhua; (19 pag.)CN108276294; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 4-Bromo-2-fluorobenzotrifluoride

Step 1: N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide and N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide[0359][0360]Toa solution of 4-bromo-2-fluoro-1- (trifluoromethyl) benzene (0.416 g, 1.7 mmol) in THF (3 mL) was added dropwise n-BuLi (2.5 M in hexane, 0.64 mL, 1.6 mmol) at -78 . The reaction solution was stirred for 1 hat -78 . To the reaction solution was added dropwise a solution of 2-methyl-N- (oxetan-3-ylidene) propane-2-sulfinamide (0.200 g, 1.1 mmol) in THF (7 mL) at -78 . The reaction solution was warmed slowly to room temperature and stirred for 16 h. The reaction solution was quenched with sat? d. aqueous NH4Cl (10 mL) . The mixture was extracted with EtOAc (3 x 30 mL) . The combined organic fractions was washed with brine (2 x 10 mL) , dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, usinggradient 0-70of ethyl acetatein petroleum ether as eluent. One isomer of the title compound N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.70-7.66 (m, 1H) , 7.37 (d, J 8.4 Hz, 1H) , 7.31 (d, J 11.2 Hz, 1H) , 5.10 (s, 2H) , 5.03 (d, J 7.2 Hz, 1H) , 4.87 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) . Another isomer of the title compound N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.54-7.49 (m, 3H) , 5.25-5.22 (m, 2H) , 4.88 (d, J 7.2 Hz, 1H) , 4.30 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) .

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 142808-15-9, Recommanded Product: 4-Bromo-2-fluorobenzotrifluoride

Step A: 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid (0378) Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (5000 mL), NH(i-Pr)2 (249 g, 1.20 equiv). This was followed by the addition of n-BuLi (905 mL, 1.10 equiv) dropwise with stirring in 30 min at -70 C. The resulting solution was stirred for 0.5 hr at -30 C. To this was added 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (500 g, 2.06 mol, 1.00 equiv) dropwise with stirring at -78 C. in 2 hr. The resulting solution was stirred for 2 hr at -78 C. The reaction was then poured into 1000 g of CO2(s) at -70 C. The pH value of the solution was adjusted to 3 with hydrogen chloride (2N) (1.5 mol/L). The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 301 g (50%) of 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid as a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 142808-15-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under nitrogen atmosphere, a solution of (2R,4R)-2,4-pentanediol (2.604 g, 25.0 mmol) in anhydrous N,N-dimethylformamide (DMF, 40.0 mL) was added dropwise to a suspension of sodium hydride (2.100 g, 60% in mineral oil, 52.5 mmol) in anhydrous DMF (40.0 mL) at 0 C and the reaction was stirred at 0 C for 30 min. 4-Bromo-2-fluorobenzotrifluoride (13.36 g, 55.0 mmol) in anhydrous DMF (20.0 mL) was added at 0 C. The reaction warmed to room temperature and stirred for 30 min. Then, the reaction mixture was heated to 100 C and stirred at 100 C for 12 h. After cooling to room temperature, the reaction was quenched by addition of saturated aqueous ammonium chloride. The organic phase was separated and the water phase was extracted with diethyl ether (30.0 mLx3). The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude material was purified by column chromatography (hexanes) to give the 1 (12.12 g, 88% yield)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xie, Huan-Ping; Yan, Zhong; Wu, Bo; Hu, Shu-Bo; Zhou, Yong-Gui; Tetrahedron Letters; vol. 59; 31; (2018); p. 2960 – 2964;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 142808-15-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00199] step 2: (R)-tert-butyl 2-(3 -fluoro-4-(trifluoromethyl)benzoyl)pyrrolidine- 1 -carboxylate. To a stirred solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C under nitrogen was added w-butyl lithium (7.99 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 42b (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was dried (MgS04), concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc). A close running impurity was not removed by this purification. The compound was further purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of 44.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; CHEN, Huifen; CHICARELLI, Mark, Joseph; DEMEESE, Jason; GARREY, Rustam, Ferdinand; GAUDINO, John; GAZZARD, Lewis; KAUS, Robert J.; KINTZ, Samuel; MOHR, Peter J.; MORENO, David, A.; SCHWARZ, Jacob; SIEDEM, Christopher, S.; WALLACE, Eli, M.; WO2013/20062; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 142808-15-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 28 Preparation of 1-bromo-3-fluoro-2-methyl-4-(trifluoromethyl)benzene To a stirred solution of bis(isopropyl)amine (1.383 mL, 9.87 mmol) in THF (27.4 mL) at -78 C. was added n-butyllithium (3.62 mL, 9.05 mmol). The resulting pale yellow solution was stirred at -78 C. for 15 min, warmed to 0 C. for 15 min, then recooled to -78 C. for 15 min. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (2 g, 8.23 mmol) was then added, and the resulting solution was stirred at -78 C. for 2 h. Iodomethane (0.512 mL, 8.22 mumol) was then added. The solution was allowed to slowly warm to room temperature (rt) and stirred overnight. The reaction mixture was diluted with 0.1 M hydrochloric acid (HCl) and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude brown residue was purified via flash chromatography on silica (5-30% ethyl acetate (EtOAc)/Hexanes) to yield the title compound as a clear oil (1.7 g, 80%): 1H NMR (400 MHz, CDCl3) delta 7.57-7.41 (m, 1H), 7.32-7.26 (m, 1H), 2.41 (dd, J=10.0, 8.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) delta -61.2, -105.7, -108.1; IR (thin film) 2177, 1319 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluorobenzotrifluoride, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary