Category: bromides-buliding-blocks

Reference of 34699-28-0,Some common heterocyclic compound, 34699-28-0, name is 1-(4-Bromophenyl)-1,2,2-triphenylethylene, molecular formula is C26H19Br, 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.

Into a 250 mL two-necked round-bottom flask under nitrogen was slowly added n-butyllithium (1.6 M in hexane, 7.5 mL, 12 mmol) and a THF solution (80 mL) of 1-(4-bromophenyl)-1,2,2-triphenylethene (3) (4.11 g, 10 mmol) at -78C. After stirring for 3 h, 2.4 mL of trimethylborate (20 mmol) was added into the reaction mixture. The mixture was warmed to room temperature and the reaction was terminated by adding hydrochloric acid (2 M, 10 mL) after 12 h. The mixture was then poured into water and extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. After filtration and solvent evaporation, the residue was purified by silica-gel column chromatography using n-hexane/ethyl acetate as eluent. White solid of 4-(1,2,2-Triphenylvinyl)phenylboronic acid (4) was obtained in 70% yield (2.6 g). 1H NMR (300 MHz, CDCl3), delta (TMS, ppm): 7.88 (d, 2H, J=8.1 Hz), 7.13-7.00 (m, 17H), 4.49 (s, 1H). 13C NMR (75 MHz, CDCl3), delta (TMS, ppm): 148.9, 144.2, 144.1, 144.09, 142.4, 141.4, 135.6, 133.5, 132.0, 131.6, 128.4, 128.3, 127.4, 127.2. HRMS (TOF): m/e 376.2030 (M+, calcd 376.1635).

The synthetic route of 34699-28-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY; TANG, Benzhong; HONG, Yuning; LEUNG, Wai Tung; US2013/59392; (2013); A1;,
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Application of 74586-53-1, A common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

General procedure: 3-(trifluoromethyl) benzoic acid (511mg, 2.69mmol) was stirred in a solvent of 58 dimethyl formamide (10mL).The reaction solution was added with 59 HATU (1.12g, 2.96mmol), 72 DIPEA (890mul, 5.37mmol) and the appropriate substituted aromatic amine (500mg, 2.69mmol), followed by stirring for about 8h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was concentrated to give the crude product, which was purified by silica gel column chromatography (eluting with 0-5% EtOAc in 82 petroleum ether) to afford the 110 product as a white solid (815mg, 84%).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Qi; Dai, Yang; Ji, Yinchun; Shi, Huanyu; Guo, Zuhao; Chen, Danqi; Chen, Yuelei; Peng, Xia; Gao, Yinglei; Wang, Xin; Chen, Lin; Jiang, Yuchen; Geng, Meiyu; Shen, Jingkang; Ai, Jing; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 671 – 689;,
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These common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, 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. Application In Synthesis of 1-(4-Bromophenyl)-N-methylmethanamine

General procedure: Aldehyde (3 mmol) was taken up in dry DCM (10 mL) in an oven dried round bottomed flask under an atmosphere of nitrogen. Acetic acid (1 mmol) was added and the reaction stirred at room temperature for 5 minutes. Amine (1 mmol) was then added and the reaction stirred at room temperature for 1 hour. The reaction was cooled to 0 C using an ice bath, then sodium triacetoxyborohydride (3 mmol) was added and the reaction warmed to room temperature and stirred until TLC indicated complete consumption of the amine. The reaction was quenched with saturated aqueous sodium bicarbonate solution. The organic layer was washed with three portions of saturated sodium bicarbonate, then acidified with concentrated hydrochloric acid. The organic layer was then washed with three portions of 2 M aqueous hydrochloric acid. The pH of the acidic washes was then adjusted to pH 10 using 4 M aqueous sodium hydroxide and the aqueous extracted with three portions of diethyl ether. The combined ether washes were dried with magnesium sulfate, filtered and concentrated to give crude product. The residue was then purified by flash column chromatography and sent to NKI for biological testing.

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Milne, Kirsty; Sun, Jianhui; Zaal, Esther A.; Mowat, Jenna; Celie, Patrick H.N.; Fish, Alexander; Berkers, Celia R.; Forlani, Giuseppe; Loayza-Puch, Fabricio; Jamieson, Craig; Agami, Reuven; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2626 – 2631;,
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Electric Literature of 34950-82-8, A common heterocyclic compound, 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, molecular formula is C7H7BrN2O, 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.

To a microwave vial is added R-8 (100 mg, 0.47 mmol), R-9 (44 mg, 0.047 mmol), HP(t-13u)3—-13F4 (27 mg, 0.093 mmol), Mo(CO)5 (123 mg, 0.47 mmol) and piperidine (0.14 mE, 1.4 mmol). Contents are dissolved in dioxane (3 mE) then treated with DI3U (0.14 mE, 0.93 mmol) and DIEA (0.33 mE, 1.86 mmol) and heated at 150 C. in the microwave for 30 mm. The mixture is cooled to ambient temperature then filtered through a pad of Celite, concentrated and purified by RHPEC to give Ex 3 (35 mg, 30%).

The synthetic route of 34950-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BOSANAC, Todd; BURKE, Michael J.; COOK, Brian Nicholas; DISALVO, Darren Todd; KIRRANE, JR., Thomas Martin; SHEN, Yue; US2018/354968; (2018); A1;,
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1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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. Safety of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (309.3 mg, 1.69 mmol, 1.20 equiv) in tetrahydrofuran (12 mL) was added n-BuLi (0.68 mL, 1.20 equiv, 2.5 M in hexane) dropwise at -78C. The solution was stirred for 30 min at -78C. To the resulting mixture was then added a solution of 5-bromo-2- ethylbenzaldehyde (300 mg, 1.41 mmol, 1.00 equiv) in tetrahydrofuran (3 mL) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H20 was added and the mixture was extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (1 :5 EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl(5-bromo-2-ethylphenyl)methanol as a yellow oil. MS (ES) m/z: 299.0, 301.0[M-OH]+.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
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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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2,6-difluoroaniline

General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Wei; Li, Xiaotian; Ren, Da; Sun, Susu; Huo, Jingqian; Wang, Yanen; Chen, Lai; Zhang, Jinlin; Molecules; vol. 24; 23; (2019);,
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Electric Literature of 4333-56-6, The chemical industry reduces the impact on the environment during synthesis 4333-56-6, name is Bromocyclopropane, I believe this compound will play a more active role in future production and life.

[000225j To a solution of Compound El (20 g, 96 mmol) in 1 -methyl-2-pyrrolidinone(300 mL) was added cesium carbonate (62.8 g, 193 mmol) and bromocyclopropane (24 mL,289 mmol). The mixture was stirred for 24 h while keeping the inner temperature between145 C and 155 C. After the reaction was cooled to ambient temperature, the dark solutionwas diluted with water (400 mL) and extracted with a mixture of ethyl acetate in petroleumether (15% v/v) (300 mL x 3). The combined organic phases were washed with brine (150mL x 4), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude product. The crude product was purified with flash column chromatography on silica gel (petroleum ether) to furnish Compound E2. HPLC: Rt: 1.96 minute. ?H-NMR (CDC13, 400 MHz): 5 (ppm) 0.80-0.88 (m, 4H), 3.67-3.82 (m, 1H), 7.15 (d, J 8.8 Hz, 1H), 7.32 (dd, J 8.8, 2.4 Hz, 1H), 7.47 (d, J 2.4 Hz, 1H).

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, Bromocyclopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; WO2015/65937; (2015); A1;,
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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 25017-13-4 as follows. Application In Synthesis of 1-(2-Bromoethyl)-3-fluorobenzene

Example 5 3-Fluorophenethyl Cyanide (24) 3-Fluorophenethyl bromide (23, 1.00 g, 12.3 mmol) was diluted in dry DMF (25 mL). Sodium cyanide (1.06 g, 61.6 mmol) was added in one portion, and the mixture was heated to 60 C. under argon for 16 h. The mixture was cooled and concentrated, and the residue was partitioned between EtOAc and H2O (50 mL each). The layers were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The organic layers were washed with H2O and sat. aq. NaCl (50 mL each), dried over anhydrous sodium sulfate, and concentrated. The resulting oil was purified by flash column chromatography (SiO2), eluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes to yield the desired product as a colorless oil (0.638 g, 87%). 1H-NMR (500 MHz; CDCl3): delta 7.31 (td, J=7.9, 6.0 Hz, 1H), 7.03-6.93 (m, 3H), 2.96 (t, J=7.4 Hz, 2H), 2.63 (t, J=7.4 Hz, 2H)

According to the analysis of related databases, 25017-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Silverman, Richard B.; Cinelli, Maris A.; US2015/210644; (2015); A1;,
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Synthetic Route of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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.

General procedure: To a well stirred solution of compound 6a or 6b (0.2 g, 1 Eq.) in absolute ethanol (10 mL), the appropriately substituted anilines(1.1 Eq) was added and the reaction mixture was refluxed for 2-3 h until TLC showed full consumption of starting materials. The excess of solvent was evaporated under reduced pressure to yield the crude solids, which were further purified by recrystallization with methanol to afford the desired title compounds (7-43).

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

Reference:
Article; Cherukupalli, Srinivasulu; Chandrasekaran, Balakumar; Kry?tof, Vladimir; Aleti, Rajeshwar Reddy; Sayyad, Nisar; Merugu, Srinivas Reddy; Kushwaha, Narva Deshwar; Karpoormath, Rajshekhar; Bioorganic Chemistry; vol. 79; (2018); p. 46 – 59;,
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74586-53-1, name is 3-Bromo-5-methylaniline, 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 3-Bromo-5-methylaniline

Intermediate 5 N-(3-Bromophenyl)cyclohexanecarboxamide [00398] Cyclohexanecarbonyl chloride (61.4 g, 419 mmol) was added to a solution of 3- bromoaniline (60 g, 349 mmol), DMAP (4.26 g, 34.9 mmol), TEA (70.6 g, 698 mmol) in DCM (400 mL) at 0 C. The mixture was slowly warmed to 15 C and stirred for 14 h. Water (200 mL) was added, and the mixture was extracted with DCM (3 x300 mL). The combined organic phases were washed with brine (2×300 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by recrystallization from MTBE (200 mL) to give N-(3- bromophenyl)cyclohexanecarboxamide (90 g, 85%) as a red brown solid. MS: 282.1 [M+H]+. The Intermediates below were synthesized from the appropriate amines following the procedure described for Intermediate 5. Note: DMAP was not used for the above Intermediates; reaction time: 2-16 h. *Acetonitrile was used as a solvent instead of DCM.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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