Month: October 2020

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 1435-51-4 as follows. 1435-51-4

Example 23-Difluoromethyl-5-(2,3-difluoro-6-nitrophenoxy)benzonitrile (FIGURE 2;ROUTE B).step 7; – /?-Methoxybenzyl alcohol (12.4 kg, 89.8 mol) was added slowly to a mixture of potassium tert-butoxide (10.0 kg, 89.4 mol) in THF (78 L) allowing the reaction exotherm to raise the temperature to ca. 35 C. After stirring at 35 to 40 C for 0.5 h, 25 (21.4 kg, 84.3 mol) was added slowly allowing the reaction to exotherm to reach ca. 60 0C. After stirring at 60 C for 2 h the reaction was monitored by hplc. After cooling to RT, HOAc (ca. 600 g) and then water (30 L) was added and the phases separated. The aqueous phase was extracted with EtOAc (20 L) and the combined organic phases washed with a mixture of saturated brine (10 kg) and water (10 L). The organic phase was concentrated in vacuo (ca. 27 inches Hg, jacket temperature ca. 65 0C) to afford an oil. MeOH (ca. 43 kg) was added to form a biphasic mixture which was aged at 45 to 50 C. The product precipitated and the slurry was stirred until a uniform consistency was achieved. After cooling to RT, and aging overnight, the product was filtered off, washed with MeOH (9.8 kg), and dried under vacuum at 50 C to afford 26.06 kg of 40. The material remaining in the reactor and filter was dissolved in THF (ca. 10 L) and the solution evaporated to dryness on a rotary evaporator to afford an additional 3.44 kg (94% overall)

According to the analysis of related databases, 1435-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/145563; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Dissolve 2,4,5-trifluorobromobenzene (10.5 g 49.8 mmol) in tetrahydrofuran (25 mL) with methyl tert-butyl ether(25 mL), cooled to -30 C, isopropyl magnesium chloride (4.8 g 46.5 mmol) was slowly added dropwise to the solution, stirred at -30 C for 10 min, and added with cuprous chloride (1.6 g 16.6 mmol). After stirring at -30C for 15 min, the compound of formula 3 (6.1 g 33.2 mmol) was dissolved in methyl tert-butyl ether (20 mL) and slowly added dropwise to the reaction system. The temperature rose from -30C to -3C within 3 h. At 10C, it was warmed to -5C over a further 3 h and reacted overnight at 0C. Saturated ammonium chloride (25 mL) was added to the reaction system, extracted with ethyl acetate (20 mL*1), washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and stirred with petroleum ether (50 mL) to obtain 15.6 g. Product 4, yield 90%.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heding (Nanjing) Pharmaceutical Co., Ltd.; Li Wensen; (18 pag.)CN105017081; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 54879-20-8, name is 2-Bromo-3-methylaniline, molecular formula is C7H8BrN, 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. 54879-20-8

EXAMPLE 7 Preparation of 7-methyl-8-bromo-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride STR33 2-Bromo-3-methylphenylhydrazine hydrochloride (23 g) was prepared as described for 2-bromo-4-methylphenylhydrazine hydrochloride in Example 4, except using 2-bromo-3-methylaniline as starting material. STR34 6-Methyl-7-bromotryptamine hydrochloride was prepared (2.42 g) as described for 5-methyl-7-bromotryptamine hydrochloride in Example 4, except using 2-bromo-3-methylphenylhydrazine hydrochloride as starting material. STR35 A suspension of azalactone (prepared as described in Example 1) (3.63 g, 14.7 mmol.) and 6-methyl-7-bromotryptamine hydrochloride (4.25 g, 4.21 mmol.) in 1N HCl (150 mL) was heated to reflux for 18 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, neutralized with saturated aqueous potassium carbonate solution and extracted with chloroform. The combined organic layers were concentrated under reduced pressure and the residue chromatographed on silica gel (ethyl acetate/0.2percent NH4 OH as eluent). The fractions containing product were pooled and concentrated under reduced pressure. The residue was dissolved in ethyl acetate containing 1percent methanol and treated with dry HCl.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54879-20-8, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5635528; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4. 51437-00-4

In the case of Q10-Br, the desired 2-fluoro-5-phenyl-toluene (S1=F) was prepared from phenylboronic acid and 2-fluoro-5-bromo-toluene via a Suzuki reaction, analogously to procedure A2. See scheme A3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-Bromo-1-fluoro-2-methylbenzene.

Reference:
Patent; Duphar International Research B.V.; US6225312; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

202865-83-6,Some common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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.

A solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), 1-bromo-3- fluoro-5-methylbenzene (23 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2003 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H20 (4:1, 2.1 mL) was heated at 85 C for 18 hours. LiOH (12.4 mg, 0.52 mmol) was added and the reaction was heated at 90 O under microwave radiation for 45 minutes. 1 N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of NH4CO2H) (60 to 80%). The product was lyophylised and afforded the title compound (13 mg, 0.024 mmol, 24%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 2.0 Hz, 1H), 8.02 (dd, J= 8.5, 2.0 Hz, 1H), 7.75 (d, J= 8.5 Hz, 1H), 7.13 (5, 1H), 7.11 (d, J= 9.9 Hz, 1H), 7.07 (d, J= 9.7 Hz, 1H),3.35 (hept, J= 6.7 Hz, 1H), 2.36 (5, 3H), 2.31 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz):536.0 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methylbenzene, its application will become more common.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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 2606-51-1 as follows. 2606-51-1

General procedure: Benzyl bromide (1 g) in dry toluene (15 mL). To this tripheylphosphine (1.5 g) was added and the reaction mixture was refluxed for 1-3 h at 120 C to get the wittig salt as precipitate. It was filtered and washed with dry benzene (yield 62-87%).

According to the analysis of related databases, 2606-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parihar, Swati; Kumar, Amit; Chaturvedi, Amit K.; Sachan, Naresh Kumar; Luqman, Suaib; Changkija, Bendangla; Manohar, Murli; Prakash, Om; Chanda; Khan, Feroz; Chanotiya; Shanker, Karuna; Dwivedi, Anila; Konwar, Rituraj; Negi, Arvind S.; Journal of Steroid Biochemistry and Molecular Biology; vol. 137; (2013); p. 332 – 344;,
Bromide – Wikipedia,
bromide – Wiktionary

626-40-4, 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. 626-40-4, name is 3,5-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

Compound II (2.25 g, 10 mmol),Compound III (2.51 g, 10 mmol) andDiisopropylethylamine (DIPEA, 3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene,Then heated to reflux under nitrogen,Until the reaction is complete (usually 5 hours).The reaction mixture was carefully poured into 200 mL of ice water,Stirred, extracted with 50 mL x 3 CH2Cl2,Combined extraction phase,Washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL), and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration and the filtrate was evaporated to dryness on a rotary evaporator to give compound IV, a white solid,

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN106749368; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

344-03-6, 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 344-03-6 as follows.

Unitine , 4 -bromotetrafluorobenzene, 0.11 muM 1 unitunitunito-cyanophenylboronic acid 0.1 muM 4 – 0 . 001molPd under a nitrogen atmosphere2(Dba)3Unitunitunits, 0.002 muM s-phos, 0 . 2molK3PO4The unitz reacted 300 ml 12h. 100 ml was found in a mixed solution consisting of unit_transformants ‘-type 100 C’-type ‘.’. Obtained M1

According to the analysis of related databases, 1,4-Dibromotetrafluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Tsinghua University; Duan Lian; Zhang Dongdong; Song Xiaozeng; Gao Wenzheng; Huang Xinxin; (33 pag.)CN110066227; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1647-26-3 name is 1-Bromo-2-cyclohexylethane, 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. 1647-26-3

Combine 6- (4-Piperidin-3-yl-phenoxy)-nicotinamide (free base compound of example 322) (0.0255g, 0.0858 MMOL), 1-BROMO-2-CYCLOHEXYLETHANE (0.0150 mL, 0.0958 mmol), and potassium carbonate (0.0245 g, 0.177 mmol) in dimethylformamide (1.0 mL) and stir for 10 min. Purify the reaction mixture by ion exchange chromatography (SCX resin, METHANOL- 2 M AMMONIA/METHANOL) and silica gel chromatography (15: 1 No. 10: 1 ethyl acetate: methanol) to provide 0.0146 g (42%) of the title compound as an off-white foam: high resolution mass spectrum (electrospray): m/z calc for C25H34N302 408. 2651, found 408.2661 ; H NMR (methanol-d4): 8.61 (s br, 1H), 8. 28 (d, 1H, J= 7.8 Hz), 7.36 (d, 2H, J= 7.8 Hz), 7.12 (d, 2H, J= 7.8 Hz), 7.01 (d, 1H, J = 8.3 Hz), 3.07 (d, 2H, J = 10.2 Hz), 2.89 (t, 1H, J= 11.2 Hz), 2.55-2. 42 (M, 2H), 2.15-1. 93 (m, 4H), 1.93-1. 64 (m, 8H), 1.63-1. 43 (m, 4H), 1.40-1. 15 (m, 8H), 1.07-0. 86 (m, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/26305; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, Adding some certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 22385-77-9.

General procedure: To a solution of phthalimide (20 mmol) in CH2Cl2 (70 mL) was added the Grignard reagent (preformed from 50 mmol ArBr, 60 mmol mg in 30 mL THF) at room temperature. The resulting mixture was stirred at room temperature for 1.5 h and quenched with saturated aqueous solution of NH4Cl (40 mL). Then the mixture was extracted with ethyl acetate and washed with brine. The collected organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography, eluting with ethyl acetate/petroleum ether 1:1 (v/v), to afford the 3-aryl-3-hydroxyisoindolin-1-ones.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 22385-77-9.

Reference:
Article; Ge, Chen; Liang, Ren-Xiao; Liu, Ren-Rong; Xiang, Bin; Jia, Yi-Xia; Tetrahedron Letters; vol. 58; 2; (2017); p. 142 – 144;,
Bromide – Wikipedia,
bromide – Wiktionary