Month: December 2020

Related Products of 10485-09-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 10485-09-3 as follows.

(3) Synthesis of 2-(1H-indene-2-yl)naphthalene Finally, 2.7 g (13.8 mmol) of 2-bromoindene was added to a 100 mL Schlenk flask, and dissolved in a mixed solution of 60 mL of DME (dimethyl ether) and 20 mL of water. 3.4 g (18 mmol) of 2-naphthalene boronic acid and 2.8 g (21 mmol) of K2CO3 were added thereto, and argon gas was bubbled therein for 10 min to remove oxygen in the solvent. Thereafter, heating was initiated under an argon atmosphere, and when the temperature reached 90 C., 800 mg (0.7 mmol, 5 mol %) of palladium(0)tetrakis(triphenylphosphine) (Pd/C) was added thereto, and stirred for 6 h. Thereafter, the reaction mixture was cooled to room temperature, and 200 mL of water was poured thereto to filter the resulting brown precipitate, which was washed with about 50 mL of ether, and then dried, thereby obtaining 2.4 g (67%) of a white solid. 1H NMR (500 MHz, CDCl3): delta 3.96 (2H, s), 7.23 (1H, m), 7.31 (1H, m), 7.48-7.54 (4H, m), 7.69-7.74 (1H, m), 7.76-7.83 (4H, m), 8.01 (1H, s).

According to the analysis of related databases, 10485-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG CHEM, LTD.; KIM, Se Young; CHO, Min Seok; KIM, Dae Hwan; LEE, Sung Min; PARK, Sung Ho; LEE, Ki Soo; HONG, Bog Ki; LEE, Yong Ho; CHO, Kyung Jin; HAN, Chang Woan; PARK, Jin Young; (13 pag.)US2016/194422; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2,3,4-trifluorobenzene

Step 1: 5-bromo-2,3,4-trifluorobenzoic acid To a solution of diisopropylamine (10.14 g, 100.20 mmol) in THF (100 mL) was added n-BuLi (40.08 mL, 2.5 M in hexane, 100.20 mmol) at -78 C. under nitrogen atmosphere. The stirring was maintained at this temperature for 1 h. Then a solution of 1-bromo-2,3,4-trifluorobenzene (17.62 g, 83.50 mmol) in THF (120 mL) was added. After stirring for 1 h at -78 C., the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl and pH was adjusted to 1-2. The mixture was extracted with ethyl acetate (100 mL*3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (20.12 g, 94.5% yield). 1H NMR (400 MHz, DMSO-d6): delta 13.95 (s, 1H), 7.97 (m, 1H).

According to the analysis of related databases, 176317-02-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIANJIN BINJIANG PHARMA, INC.; Tian, Hongqi; Ji, Conghui; Liu, Chunlei; Kong, Li; Cheng, Ying; Huang, Gongchao; US2014/371278; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(4-Bromophenyl)cyclopropanamine

Step 1: tert-butyl (l-(4-bromophenyl)cyclopropyl)carbamate: A stirred solution of l-(4- bromophenyl)cyclopropanamine (1.00 g, 4.72 mmol) in DCM (10 ml) was treated with B0C2O (1.08 g, 4.95 mmol) and the resultant mixture stirred overnight. The solution was diluted with DCM (20 ml), was washed with brine (20 ml) and filtered through a phase separation cartridge. The filtrate was concentrated in vacuo to afford the title compound (1.43 g, 4.50 mmol, 98% purity) as a white solid. 1H NMR (400 MHz, Chloroform-d) (two rotamers in a 3: 1 ratio) delta 7.44 – 7.36 (m, 2H), 7.10 (d, / = 8.3 Hz, 2H), 5.22 (br s, 1H, major), 5.01 (br s, 1H, minor), 1.43 (br s, 9H), 1.32 – 1.11 (m, 4H).

According to the analysis of related databases, 345965-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BERGENBIO AS; SHIERS, Jason John; WATTS, John Paul; ONIONS, Stuart Thomas; QUDDUS, Mohammed Abdul; WRIGGLESWORTH, Joseph William; SAMBROOK-SMITH, Colin Peter; NAYLOR, Alan; LONDESBROUGH, Derek; (444 pag.)WO2016/102672; (2016); A2;,
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. 7745-91-7, name is 3-Bromo-4-methylaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrN

A cooled (0 0C) solution of 3-bromo-4-methylaniline (ABCR; 1.00 g; 5.37 mmol) in pyridine (20 ml) was treated with methanesulfonyl chloride (500 mul; 6.45 mmol). The reaction mixture was allowed to warm to RT and stirred for 1 hour, then EtOAc was added and the organic layer was washed with a 1 N aqueous solution of HCI. The organic layer was dried over MgSO4, filtered and concentrated to dryness to give the title compound as a brown solid (1.42 g, quantitative).1H NMR (300MHz, DMSO-d6) delta [ppm] 9.81 (1 H, s), 7.40 (1 H, d, J= 2.1 Hz), 7.31 (1 H, d, J= 8.3 Hz), 7.13 (1 H, d, J= 8.3 Hz, J= 2.1 Hz), 2.99 (3H, s), 2.29 (3H, s)

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; CLEVA, Christophe; PRETRE, Adeline; WO2010/92043; (2010); A1;,
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. 69321-60-4, name is 2,6-Dibromotoluene, A new synthetic method of this compound is introduced below., Recommanded Product: 69321-60-4

A mixture of 1,3-dibromo-2-methylbenzene (6.0 g, 24 mmol), phenylboronic acid(2.9 g, 24 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexedwith dichloromethane (1: 1) (817 mg, 1. 0 mmol) and potassium carbonate (1 0 g, 725 mmol) in 1,4-dioxane (100 mL) and water (70 mL) was stirred at room temperatureovernight. The reaction was quenched with water, and extracted with ethyl acetate (3x 150mL). The combined organic layers were washed with brine, dried over Na2S04, filtered andconcentrated under reduced pressure. The residue was purified by chromatography on silicagel, eluting with 0-5% EtOAc/hexanes, to give the desired product (4.7 g).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; QIAN, Ding-Quan; WU, Liangxing; YAO, Wenqing; (103 pag.)WO2017/205464; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 66417-30-9, 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. 66417-30-9 name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, 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.

2-Bromo-4- (trifluoromethyl) toluene (23b, 5g, 21 mmol) was placed in round-bottom flask and dissolved in 150 ml DMF.Then KOAc (6.2g, 63 mmol, 3eq) was added to the reaction mixture in one portion followed by addition of PdCl2 (dppf)(0.46g, 0.63 mmol, 0.03eq) and Bis (pinacolato) diboron 5.9g,23.1 mmol, l.leq). The solution was stirred at 80C for 48h. Then the solvent was removed and the black residue was subjected to plug column chromatography (EtOAc) resulting in dark green oily residue. The compound was further purified by second column chromatography (2% MeOH/DCM) .Pure product (3.5g, 58%) as a slightly green oil was collected.Structure determination:RP-HPLC Conditions: HP 1100 HPLC chromatograph, Waters 3.9 x 150 mm NovaPak HR C18 column with guard column, 0.010 mL injection, 1.5 mL/min, 1.500 mL injection loop, 254 nm detection, A = water (0.1% v/v TFA) and B = MeCN (0.1% v/v TFA), gradient 10% B 1 min, 10-80% B over 9 min, 80-100% B over 1 min, 100 %B 1 min, retention time 7.9 min (for boronic acid) and 12.6 min (for pinacol ester). 1H NMR (400 MHz, CDCl3): delta 1.35 (s, 12H), 2.58 (s, 3H), 7.26 (d, IH), 7.55 (d, IH), 8.00 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SENSORS FOR MEDICINE AND SCIENCE, INC.; WO2008/66921; (2008); A2;,
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. 2550-36-9, name is (Bromomethyl)cyclohexane, A new synthetic method of this compound is introduced below., Recommanded Product: (Bromomethyl)cyclohexane

After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.47 ml of (bromomethyl)cyclohexane (Aldrich) was added, and 0.5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at 60 C. for 2 hours, the temperature was again lowered to room temperature, and then the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) and then dried to obtain 787 mg of a compound (yield: 99%). 400 mg of the obtained compound was dissolved in 5 ml of dichloromethane, and 0.14 ml of methyl hydrazine (TCI) was slowly added at 0 C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0 C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 240 mg of a solid (yield: 94%). 21 mg of the obtained solid and 50 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80 C. for 4 hours. After the temperature was lowered to room temperature, the reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1103 (50 mg, yield: 82%). 1H-NMR (400 MHz, CDCl3) delta 5.87-5.78 (m, 2H), 5.35-5.34 (m, 1H), 5.29-5.26 (m, 1H), 5.16 (m, 1H), 4.24-4.14 (m, 3H), 3.86-3.76 (m, 2H), 3.58-3.51 (m, 1H), 2.41-0.61 (m, 46H)

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kwon, Young-Gune; Suh, Young-Ger; US2014/378399; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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. Formula: C7H6BrF

0.867 g (35.67 mmol) of magnesium turnings were dried and suspended in 17 ml of anhydrous THF under argon. A solution of 1 ,2-dibromoethane (0.14 ml, 1.62 mmol) and 2-bromo-6-fluoro-toluene (6.74 g, 35.67 mmol) in 17 ml of anhydrous THF was then added dropwise so as to maintain a gentle reflux. Once the magnesium had been consumed, copper(l) iodide (0.432 g, 2.27 mmol) was then added, followed by a solution of epichlorohydhne (3.00 g, 32.42 mmol) in DMF (8 ml). The mixture was stirred for 3.5 h at room temperature and then quenched with a saturated solution of ammonium chloride (120 ml). The organic layer was separated, and the aqueous phase was extracted twice with EA. The combined organic phases were washed twice with a saturated solution of ammonium chloride, dried over sodium sulfate, filtered and evaporated to dryness. The product was purified by chromatography on silica gel (cyclohexane/EA, from 100:0 to 90:10) to give 6.89 g of 1-chloro-3-(3-fluoro- 2-methyl-phenyl)-propan-2-ol. 3.92 g (16.23 mmol) of this alcohol were dissolved in DCM under argon, and 1 ,1 ,1-thacetoxy-1 ,1 -dihydro-1 ,2-benziodoxol-3(1 H)-one (Dess-Martin periodinane reagent; 7.57 g, 16.23 mmol) was added. The mixture was stirred at room temperature overnight and then diethyl ether (150 ml) was added. The mixture was washed three times with 1 N hydrochloric acid (70 ml) and twice with a saturated solution of sodium chloride, and extracted with ether. The extracts were dried over sodium sulfate, filtered and evaporated to dryness. 2.69 g of the title compound were obtained as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1422-54-4, its application will become more common.

Reference:
Patent; SANOFI-AVENTIS; STEINHAGEN, Henning; SCHEIPER, Bodo; MATTER, Hans; MCCORT, Gary; BEGIS, Guillaume; GOBERVILLE, Pascale; THIERS, Berangere; WO2011/12538; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1422-53-3,Some common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, molecular formula is C7H6BrF, 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.

The compound of formula 3 (5.0 g, 26.5 mmol, 1.0 equiv) and 98% concentrated sulfuric acid (50 ml) were added to a 100 ml three-necked flask.The solution was cooled to 0 C to 5 C and potassium nitrate (3.5 g, 34.6 mmol, 1.3 equiv) was added in portions.And reacted at 25 C for 2 hours under nitrogen protection. After completion of the reaction, the reaction solution was poured into a large amount of ice water,Ethyl acetate extraction. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, Concentrate under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether) to give 3.4 g of the compound of formula 4 as a yield of 54.3%.

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

Reference:
Patent; Shanghai Acebright Pharmaceuticals Group Co., Ltd.; Yu, Libing; Guo, Maojun; Yang, QinGang; Liu, Huixin; (23 pag.)CN105646333; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103-64-0, A common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

At room temperature,To the appropriate amount of the organic solvent DMF was added 100 mmol of the compound of the above formula (I)250 mmol of the compound of formula (II)4 mmol of catalyst (1 mmol of Pd (TFA) 2 with 3 mmol of Cu (acac) 2)35 mmol of 1-ethyl ethyl ether-3-methylimidazolebis (trifluoromethanesulfonyl) imide salt and 250 mmol of triisopropanolamine,Then heated to 70 C,And the reaction was stirred at that temperature for 8 hours; After the reaction,The resulting mixture was filtered while hot,To obtain a filtrate;To the filtrate was added a 10% hydrochloric acid solution with a mass percentage of 10%Adjust the pH to neutral;Then ethyl acetate,Oscillation extraction 2-3 times,Combined organic phase,Dried over anhydrous magnesium sulfate,Then concentrated under reduced pressure,The resulting residue was subjected to 200-300 mesh silica gel column chromatography,The petroleum ether-n-butanol mixture was used as the eluent,Wherein the volume ratio of petroleum ether to n-butanol is 9: 1,Thereby obtaining a compound of the above formula (III)The yield was 97.3%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Qingdao University; Xia Yunqiu; Zhou Yingbin; Wang Yanxin; Zhong Weizhen; Guo Shenbo; (9 pag.)CN104803912; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary