Month: September 2021

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. 52548-00-2, name is 1-Bromo-4-fluoro-2,3-dimethylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H8BrF

To a 250 ml-round bottle flask equipped with magnetic stir bar were added 1- Boc-piperizine (2.5 g, 13.42 mmol), 1-bromo-4-fluoro-2,3-dimethylbenzene (3.27 g, 16.11 mmol), Cs2CO3 (13.12 g, 40.3 mmol), and RuPhos Pd G2 (1.043 g, 1.342 mmol). To the mixture was charged dioxane (67.1 ml) at RT under N2. The mixture was stirred at RT while flushed with N2 for about 5 min and then warmed up to 90 C. The mixture was stirred at 90 C overnight. The mixture was cooled to RT, and partitioned between EtOAc and water (100 ml x 50 ml). The aqueous was extracted with EtOAc for three times (100 ml x 3). Organic phases were combined and washed with sat. NaCl, separated and dried over Na2SO4, filtered, concentrated, and followed by normal phase purfication (Isco system, 120 g Isco, RediSep gold column, 0-100% EtOAc / hexane as eluting solvent) to afford the title compound as a solid. LCMS m/z (M+H): 309.67

The synthetic route of 52548-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane; CHEN, Ping; FRADERA, Xavier; GUO, Liangqin; HAN, Yongxin; HE, Shuwen; HUANG, Xianhai; KOZLOWSKI, Joseph; LI, Guoqing; MARTINOT, Theodore, A.; PASTERNAK, Alexander; VERRAS, Andreas; XIAO, Li; YU, Wensheng; ZHANG, Rui; (267 pag.)WO2020/112581; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 59734-92-8,Some common heterocyclic compound, 59734-92-8, name is 1-Bromo-2-cyclohexylbenzene, molecular formula is C12H15Br, 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 a solution of CuI (19 mg, 0.10 mmol) and NaI (0.6 g, 4.0 mmol) in pentanol (3 niL) was added (18 mg, 0.2 mmol) and l-bromo-2- cyclohexylbenzene (0.48 g, 2.0 mmol). The mixture was purged for 5 min with argon and heated overnight at reflux. The resulting mixture was purified by silica gel chromatography using hexanes to afford the title compound as clear oil (0.51 g, 90%).[0132] 1H NMR (500 MHz, CDCl3): delta 1.21-1.30 (m, IH), 1.33-1.53 (m, 4H), 1.76-1.90 (m, 5H), 2.77 (tt, J = 11.7, 3.1 Hz, IH), 6.86 (td, J = 7.7, 1.6 Hz, IH), 7.20 (dd, J= 7.8, 1.6 Hz, IH), 7.27 (q, J = 7.5 Hz, IH), 7.81 (d, J = 7.9 Hz, IH)

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-2-cyclohexylbenzene, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/55674; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 201138-91-2,Some common heterocyclic compound, 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, molecular formula is C12H6Br2O, 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.

Under an argon atmosphere, to a 1,000 ml Erlenmeyer flask, 4,6-dibromodibenzofuran (16.3 g, 50 mmol), phenylboronic acid (6.71 g, 55 mmol), K2CO3 (20.7 g, 150 mmol), Pd(PPh3)4(2.89 g, 2.5 mmol), 500 ml of a mixture solution of toluene/EtOH/H2O (4/2/1) were added in order, followed by heating and refluxing at a temperature of about 80 C. for about 5 hours. Then, the reaction mixture was cooled to room temperature, and toluene was added thereto. An aqueous layer was removed, and an organic layer was washed with a saline solution and dried with MgSO4. MgSO4 was filtered and separated, and an organic layer was concentrated. The crude product thus obtained was separated by silica gel column chromatography (using a mixture solvent of hexane/toluene) and recrystallized to obtain Intermediate A as a white solid (12.1 g, yield 75%). The structure of the product was identified using FAB-MS (m/z=323).

The synthetic route of 201138-91-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Display Co., Ltd.; UNO, Takuya; (209 pag.)US2019/165285; (2019); 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. 2550-36-9, name is (Bromomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H13Br

[0307] A four-necked reactor equipped with a thermometer was charged with 3.00 g (18.2 mmol) of 2-hydrazinobenzothiazole and 30 ml of DMF under a nitrogen stream to prepare a homogeneous solution. After the addition of 7.55 g (54.6 mmol) of potassium carbonate and 3.86 g (21.8 mmol) of (bromomethyl)cyclohexane to the solution, the mixture was stirred at 80C for 9 hours. After completion of the reaction, the reaction mixture was cooled to 20C, added to 300 ml of water, and extracted with 500 ml of ethyl acetate. After drying the ethyl acetate layer over anhydrous sodium sulfate, sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a yellow solid. The yellow solid was purified by silica gel column chromatography (n-hexane:ethyl acetate=85:15 (volume ratio)) to obtain 2.36 g of an intermediate S as a white solid (yield: 49.7%). [0308] The structure of the target product was identified by 1H-NMR. [0309] 1H-NMR (400 MHz, CDCl3, TMS, delta ppm): 7.58 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.1 Hz), 7.26 (dd, 1H, J=7.0 Hz, 8.1 Hz), 7.04 (dd, 1H, J=7.0 Hz, 8.0 Hz), 4.24 (s, 2H), 3.59 (d, 2H, J=7.4 Hz), 1.84-1.92 (m, 1H), 1.67-1.77 (m, 5H), 1.16-1.29 (m, 3H), 1.02-1.13 (m, 2H).

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 2550-36-9.

Reference:
Patent; Zeon Corporation; SAKAMOTO Kei; OKUYAMA Kumi; EP2703385; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 445-02-3,Some common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

Isopentyl nitrite (0. 67ML) was added dropwise to a solution of 4-bromo-2- (trifluoromethyl) aniline (1.2g) and dimethyl sulfide (0. 45ML) in acetonitrile (12ML). The reaction was slowly heated to reflux and then refluxed until gas evolution ceased. The volatiles were evaporated, the residue absorbed onto silica and the product eluted off with isohexane. YIELD 0. 8G. 1H NMR DMSO-d6: 8 7.59 (dd, 2H), 7.23 (d, 1H), 2.51 (s, 3H)

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-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 7745-91-7, 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. 7745-91-7 name is 3-Bromo-4-methylaniline, 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.

Method 8; JV-(3-Bromo-4-methylphenylV3-(trifluoromethyl>)benzaniide3-(Trifluoromethyl)benzoyl chloride (0.78 ml, 5.2 mmol) was added to a stirring solution of 3-bromo-4-methylaniline (0.74 g, 4.0 mmol) and triethylamine (1.65 ml, 12 mmol) in 15 ml DCM. The mixture was stirred at 25 0C for 4 h. The reaction mixture was washed with 1 N HCl, 10 % NaOH, water and brine. The combined organics were dried and concentrated under reduced pressure. The resulting residue was used without further purification; m/z 359

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/79791; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7617-93-8, 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. 7617-93-8, name is 2-Bromo-1,4-bis(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 30 1-[2,5-bis(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 2,5-bis(trifluoromethyl)phenyl bromide (4.45 g), 3-hydroxypyrrolidine (1.2 g), palladium(II) acetate (0.16 g), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.87 g) and cesium carbonate (13.6 g) in toluene (74 mL) was stirred under an argon gas atmosphere at 80C for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10 – 75:25) to give the title compound (3.79 g, yield 91%) as an orange oil. 1H-NMR (300 MHz, CDCl3)delta:1.72 (d, J = 4.9 Hz, 1 H), 1.95 – 2.10 (m, 1 H), 2.10 – 2.24 (m, 1 H), 3.21 – 3.43 (m, 2 H), 3.60 – 3.78 (m, 2 H), 4.48 – 4.65 (m, 1 H), 7.01 – 7.16 (m, 1 H), 7.16 – 7.23 (m, 1 H), 7.63 – 7.74 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,4-bis(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-51-4,Some common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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 4.; (4- (3-bromo-5-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine (enantiomer 2); Dissolve 1, 3-dibromo-5-fluoro-benzene (19.8 g, 77.90 mmol) in dry diethyl ether (300 mL) and cool to-60C. Add 1.6M n-BuLi in hexanes (50.9 mL, 81.44 mmol) dropwise over 15 min. and stir an additional 15 min. Add a pre-cooled (-60C) solution of 4-dimethylamino-cyclohexanone (10.0 g, 70.8 mmol) in diethyl ether (200 mL) dropwise over 30 min. Stir at-60C to-20C for 2 hr. , then warm to ambient temperature and stir for 1 hr. Quench the reaction with water (200 mL) and extract with ethyl acetate (3 x 200 mL). Dry over sodium sulfate, filter and concentrate. Purify the residue by flash chromatography (15% 2M NH3/MeOH in DCM) to obtain 1- (3-Bromo-5- fluoro-phenyl) -4-dimethylamino-cyclohexanol as a white foam (14. 5 g, 64.8%). MS (ES) m/z = 316 (M-H)-, 318 (M+H) +, 1H NMR (CDC13) : 8 7.41 (d, 1H, J= 2 Hz), 7.15 (m, 2H), 2.3 (m, 8H), 1.78 (m, 8H). Combine 1- (3-bromo-5-fluoro-phenyl)-4-dimethylamino-cyclohexanol (14.5 g, 45.9 mmol), p-TsOH (21.8 g, 114.6 mmol) and toluene (200 mL) and heat to reflux for 3 hr. Cool to ambient temperature and partition between ethyl acetate (500 mL) and 1M NaOH solution (250 mL). Wash the organic layer with 1M NaOH solution (200 mL) and saturated aqueous NaCl (200 mL), dry over sodium sulfate, filter and concentrate. Purify the residue by chromatography (silica gel, 10% 2M NH3/MeOH in DCM) to obtain (4- (3- bromo-5-fluoro-phenyl) -cyclohex-3-enyl) -dimethyl-amine (10.8 g, 79%): MS (ES) m/z= 298 (M-H)’, 300 (M+H) ; 1H NMR (CDC13) : 8 7.25 (d, 1H, J= 2 Hz), 7.02 (dd, 1H, J= 8 Hz, J= 2 Hz), 6.9 (dd, 1H, J= 8 Hz, J= 2 Hz), 6.04 (m, 1H), 2. 38 (m, 4H), 2.27 (s, 6H), 2.09 (m, 2H), 1.48 (m, 1H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/61439; (2005); 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. 7051-34-5, name is (Bromomethyl)cyclopropane, A new synthetic method of this compound is introduced below., Safety of (Bromomethyl)cyclopropane

L-Cysteine (100 g, 0.825 mol) was suspended in ethanol (850 mL). A solution of sodium hydroxide (1.65 mol) in ethanol (650 mL) was added during 40 min at 20-25 C. To the solution was added bromomethylcyclopropane (0.907 mol) at 25-30 C. The reaction mixture was stirred at ambient temperature overnight, the neutralized with 2N HCl (300 mL). The suspension was concentrated under vacuum to 400 mL, then water (750 mL) was added, and pH was adjusted to 6.5 with 2N HCl. The mixture was stirred for 2 h at 0-5 C., the precipitate was filtered, washed with water and dried under vacuum to give (R)-2-amino-3-cyclopropyl-methylsulfanylpropionic acid as a white crystalline solid (128.2 g; yield=88.6 %). C7H13NO2S; MW=175.3; Tmelt=2090 C; NMR (DMSO, ppm): 0.20 (m, 2H), 0.50 (m, 2H), 0.94 (m, 1H), 2.50 (m, 2H), 2.78 (dd, J=14.5 and 8.5 Hz, 1 H), 3.08 (dd, J=14.5 and 4 Hz, 1 H) and 7.64 (ls, 1H (mobile)); SM (EI; m/z): 130 (M+-COOH), 89, 74.

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; AVENTIS PHARMACEUTICALS, INC.; US2004/19218; (2004); 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. 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 86845-27-4

A mixture of 4-methyl-3-trifluorobromobenzene (33.26 g, 104.261 mmol) from step 1 above , KCN (20.43 g, 313.67 mmol) and tetrabutylammonium bromide (3.37 g, 10.45 mmol) in CH2CI2/H2O 1:1 (300 mL) was stirred at room temperature for 4 hours. The layers were separated and the organic layer washed with H2O (100 ml_) 1N HCI (100 ml_), brine, dried over Na2SO4 and then concentrated to a brown oil which was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the product as a clear oil (14.9 g, 54%). 1H NMR (400 MHz, CDCI3) 6 3.91 (s, 2H), 7.57 (d, J=8.3 Hz, 1 H), 7.75 (dd, J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).

According to the analysis of related databases, 86845-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2006/18725; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary