Month: June 2021

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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 16518-62-0

Into a 50 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.17 g, 5 mol percent) and 3-bromo-N,N-dimethylaniline (0.60 g, 3 mmol) under an argon atmosphere. Next, 10 mL of 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide (0.5 M in THF, 5 mmol) was added via a syringe. The resulting mixture was stirred at rt for 3.0 h. Quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL .x. 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20percent ethyl acetate/80percent heptane) afforded 3-(5-(1,3-dioxolan-2-yl)furan-2-yl)-N,N-dimethylaniline (1g, 0.71 g) in 92percent isolated yield.

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:
Article; Rieke, Reuben D.; Kim, Seung-Hoi; Tetrahedron Letters; vol. 52; 10; (2011); p. 1128 – 1131;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 627871-16-3, 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 627871-16-3 as follows.

A mixture of 5-bromo-4-fluoro-2-methylaniline (2.04 g, 10.0 mmol), CuCN (889 mg, 10.0 mmol) and CuI (1.9 g, 10.0 mmol) in NMP was purged with N2 for 5 minutes and then sealed and heated at 195 C. for 30 minutes under microwave condition. The mixture was subjected to standard aqueous workup to give a residue which was purified by silica chromatography to yield 5-amino-2-fluoro-4-methylbenzonitrile (51) (540 mg, 36% yield). MS m/z 151.0 (M+1)+.

According to the analysis of related databases, 627871-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; YEH, Vince; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; US2013/59846; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 630-17-1, 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 630-17-1 as follows.

Example 21; 2-tert-Butyl-l-[(4,4-difluorocycIohexyl)methyl]-5-{[4-(2,2-dimethyIpropoxy)piperidin- l-yl]carbonyl}-lH-benzimidazole; To a solution of NaH (0.017 g, 0.414 mmol) in 2 mL of DMF at 0C under nitrogen, a DMF solution (2 mL) of l-({2-ter/-butyl-l-[(4,4-difluorocyclohexyl)methyl]-lH-benzimidazol-5- yl}carbonyl)piperidin-4-ol (for preparation, see Example 16, Step B) (0.060 g, 0.138 mmol) was added dropwise. The solution was stirred at O0C under nitrogen for 30 min. 1-Bromo- 2,2-dimethylpropane (0.035 mL, 0.276 mmol) was added dropwise and the solution was stirred at 1000C overnight. The reaction was quenched at 00C by addition of aqueous saturated NaHCOs solution and the solvent was concentrated. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCC>3 solution, brine and dried over anhydrous Na2SO4. The product was purified by reversed-phase HPLC using 20-50% CH3CN/H2O and lyophilized to afford the title compound as the corresponding TFA salt. Yield: 45 mg (53%); 1H NMR (400 MHz, METHANOL-D4) delta 0.89 – 0.93 (m, 9 H), 1.51 – 1.64 (m, 2 H), 1.65 – 1.70 (m, 10 H), 1.70 – 1.85 (m, 6 H), 1.94 (s, 1 H), 2.01 – 2.12 (m, 2 H), 2.20 – 2.32 (m, 1 H), 3.14 (d, /=8.59 Hz, 2 H), 3.32 (s, 1 H), 3.54 – 3.62 (m, 2 H), 3.67 (s, 1 H), 3.93 (s, 1 H), 4.57 (d, /=7.62 Hz, 2 H), 7.62 (dd, /=8.69, 1.46 Hz, 1 H), 7.78 (d, /=0.98 Hz, 1 H), 7.99 (d, /=8.59 Hz, 1 H); MS (ESI) (M+H)+ 504.3.

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/145563; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 558-13-4,Some common heterocyclic compound, 558-13-4, name is Carbontetrabromide, molecular formula is CBr4, 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.

To an ice cold solution of the hexanol (ca. 19.8 mmoles) and carbon tetrabromide (21.98 mmoles) in methylene chloride (50 ml) was added triphenylphosphine (22.30 mmoles) in methylene chloride (50 ml) and the resulting solution was stirred for 2.5 hours. The volatiles were evaporated and the residue was taken up in ether (100 ml), cooled in ice, and filtered. The filtrate was evaporated and distilled to afford 6-phenylhexyl bromide as an oil.

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

Reference:
Patent; SmithKline Beckman Corporation; US4871771; (1989); A;,
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. 615-54-3, name is 1,2,4-Tribromobenzene, A new synthetic method of this compound is introduced below., Safety of 1,2,4-Tribromobenzene

51.34 g (484.0 mmol) of anhydrous sodium carbonate are dissolved in 171.7 ml of water. A solution of 25.0 g (79.0 mmol) of 1,2,4-tribromobenzene and 67.7 g (476 mmol) of 2-butoxy-1,2-oxaborolane in 965.2 ml of tetrahydrofuran (THF) is added, 1.65 ml (11.9 mmol) of triethylamine are added, and the mixture is stirred and degassed for 30 min. using a stream of argon. 1.40 g (7.49 mmol) of palladium(II) chloride (59% of palladium, anhydrous) and 1.85 g (3.97 mmol) of 2-dicyclohexylphoshino-2′,6′-diisopropoxy-1,1′-biphenyl are added, and the reaction mixture is stirred under reflux for 18 hours. The reaction mixture is allowed to cool to room temperature (RT), water and methyl tertiary-butyl ether (MTBE) are added, and the phases are separated. The water phase is extracted with MTBE, and the combined organic phases are washed with saturated NaCl solution, dried over sodium sulfate, filtered and evaporated in vacuo. The product is obtained as a yellowish oil and is filtered through silica gel with a mixture of ethyl acetate (EA) and methanol (9:1). The product fractions are combined and evaporated in vacuo, giving the reaction product as a pale-yellow oil. The product is characterised by means of NMR spectroscopy. 1H NMR (500 MHz, DMSO-d6) delta=1.66 (mc, 6H, CH2), 2.42-2.69 (m(superimposed with DMSO), 6H, CH2,), 3.36-3.49 (m, 6H, CH2), 4.44 (t, J=5.15 Hz, 1H), 4.48 (mc, 2H), 6.92 (dd, J=1.7, 7.72 Hz, 1H), 6.95 (d, J=1.53 Hz, 1H), 7.03 (d, J=7.7 Hz, 1H).

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; Merck Patent GmbH; ENGEL, Martin; MAAG, Sabrina; ALMEROTH, Ingo; FORTTE, Rocco; GOETZ, Achim; KODEK, Thorsten; HEPPERT, Oliver; (71 pag.)US2018/216006; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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. COA of Formula: C6H5Br2N

A solution of 2,6-dibromoaniline (1.0 g, 4.0 mmol) in CHCl3 (8 ml) was treated with a suspension of m-CPBA (2.1 g, 12.0 mmol) in CHCl3 (8 ml) and the resulting mixture stirred overnight. After 24 h the solution was diluted with CHCI3 and washed successively with sat. aq. Na2S2Os, sat. aq. NaHCO3 and brine. The organic layers were dried over Na2SO4, filtered, concentrated and dried in vacuo to afford 1,3-dibromo-2-nitrosobenzene (1.0 g, 100 %); the resultant solid was used directly in the next stage.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-30-0, its application will become more common.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 502496-36-8, The chemical industry reduces the impact on the environment during synthesis 502496-36-8, name is 3-Bromo-5-fluoro-2-methylaniline, I believe this compound will play a more active role in future production and life.

NaNO? (1.93 g, 28.0 mmol) was added to a solution of 3-bromo-5-fluoro-2-methylaniline (4.40 g, 21.6 mmol) in acetic acid (100 mL) and half-concentrated aqueous HC1 (400 mL) at 0 C. After stirring for 5 min at 0 C, CuCl (3.72 g, 37.5 mmol) was added to the reaction mixture. After stirring for 2 h at 0 C, the reaction mixture was warmed to RT and stirring was continued for additional 3 h. Subsequently, the mixture was extracted with Et?0. The combined organic layers were washed with concentrated aqueous NaHCCL-solution (1 x), dried over Na^SCL, filtered, and concentrated in vacuo (bath temperature max. 30 C, vacuum >150 mbar) to give the title compound.

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, 3-Bromo-5-fluoro-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARVARIS B.V.; GIBSON, Christoph; SAUPE, Joern; AMBROSI, Horst-Dieter; HAUSTEDT, Lars Ole; (99 pag.)WO2019/101906; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 129316-09-2, The chemical industry reduces the impact on the environment during synthesis 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, I believe this compound will play a more active role in future production and life.

Step 1 : 1-(3-Bromo-5-(te t-butyl)phenyl)ethanone (P49a) To a solution of 1 ,3-dibromo-5-(fert-butyl)benzene (664 mg, 2.22 mmol) in toluene (15 mL) were added tri-n-butyl-1-ethoxyvinyl tin (965 mg, 2.66 mmol) and Pd(PPh3)2CI2 (150 mg 0.22 mmol) under N2. The mixture was stirred at 95C for 3 h, evaporated, diluted with 1 ,4-dioxane and 2N HCI, stirred rapidly at 25C for 1h and then extracted with EA. The combined organic layers were washed with brine, dried over Na2S04, concentrated and purified by CC to afford compound P49a (310 mg, 55%).

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, 1,3-Dibromo-5-(tert-butyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, molecular formula is C12H8Br2, 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. COA of Formula: C12H8Br2

General procedure: Dibromoarene 1 (0.5 mmol), alkyne 2 (0.6 mmol), Pd(OAc)2 (5 mol%, 5.6 mg ),Xantphos (5.5 mol%,16 mg), K2CO3 (1.5 mmol, 207 mg) were added into a Schlenkflask. The flask was evacuated and backfilled with nitrogen (3 cycles). Dry DMF (5mL) was added by syringe. The mixture was heated to 120 C and stirred until thereaction finished (TLC analysis). After cooling to room temperature, the mixture wasextracted three times with ethyl acetate. The organic layers were combined and driedover Na2SO4. After filtration, the solvents were evaporated. The crude product wasfurther purified by silica gel chromatography, using petroleum ether and ethyl acetateas eluents to provide the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19190-91-1, its application will become more common.

Reference:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
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. 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were placed 4-nitrobenzoyl chloride (5g, 0.50 g 2.7 mmol), Cu2O (0.030 g, 0.21 mmol), 2,2′-bipyridyl (0.020 g, S29 0.13 mmol), and a DMF solution of 2-Zn (0.66 M, 1.0 mL, 0.66 mmol), and the whole were stirred at 100 C for 20 h. The resultant was poured into water and the organic products were extracted with Et2O three times. The combined organic layers were dried over anhydrous Na2SO4, then filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the corresponding 6g (0.14 g, 0.51 mmol) in 77% yield as a pale yellow oil.2,2,3,3-Tetrafluoro-1-(4-nitrophenyl)pent-4-en-1-one (6g) Yield: 77% (0.14 g, 0.51 mmol); Pale yellow oil (hexanes/AcOEt = 5/1, Rf = 0.50); 1H NMR (CDCl3): delta 5.78 (d, J = 11.0 Hz, 1H, cis-CH2=CH), 5.91 (dt, J = 17.31, 1.68 Hz, 1H, trans-CH2=CH), 6.07 (dtd, J = 17.3, 11.9, 11.0 Hz, 1H, CH2=CH), 8.21 (d, J = 8.4 Hz, 2H, Ar-H), 8.30-8.33 (m, 2H, Ar-H); 13C NMR (CDCl3): 111.7 (tt, J = 264.9, 37.4 Hz, CF2), 114.7 (tt, J = 250.6, 31.4 Hz, CF2), 123.9 (Ar), 125.6 (t, J = 23.9 Hz, CH2=CH), 125.6 (t, J = 9.4 Hz, CH2=), 131.4 (t, J = 3.4 Hz, Ar), 136.7 (Ar), 151.2 (Ar), 185.1 (t, J = 28.0 Hz, C=O); 19F NMR (CDCl3): -115.04 (s, 2F, CF2-C=O), -113.37 (d, J = 11.9 Hz, 2F, =CH-CF2); IR (neat): 3057, 1715, 1604, 1531, 1351, 1156, 1014, 834 cm-1 ; HRMS (FAB) calcd for C11H8F4NO3 [M+H]+ : 278.0440, found 278.0435.

The synthetic route of 18599-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary