Author: Jessica.F

Electric Literature of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,6-Dihydroxyacetophenone 7 (1.0equiv.) was dissolved in acetone (10mL) and then anhydrous potassium carbonate (2.0equiv.) with corresponding alkyl bromides (1.0equiv.) were added and the reaction mixture was stirred at 80C for overnight. After evaporating the solvent under reduced pressure the reaction mixture was further diluted with dichloromethane (20mL) and washed with water (20mL×3). The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the title compounds 8. 6.1.1.1 1-(2-(Cyclohexylmethoxy)-6-hydroxyphenyl)ethanone (8a) Yield 50%; Yellow colored solid; 1H NMR (CDCl3) delta 13.20 (s, 1H), 7.29 (t, J = 8.4 Hz, 1H), 6.53 (d, J = 8.4 Hz, 1H), 6.40 (d, J = 8.4 Hz, 1H), 3.81 (d, J = 6.0, 2H), 2.72 (s, 3H), 1.69-1.87 (m, 5H), 1.19-1.29 (m, 6H).

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Hyun-Sun; Venkateswararao, Eeda; Boggu, Pulla Reddy; Sharma, Vinay K.; Kim, Youngsoo; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4330 – 4338;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(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.

3-(1H-imidazo1-1-y1)-5-(trfluoromethy1)anh1ine: A mixture of 3-Amino-5- bromobenzotrifluoride (4.0 g, 0.0167 mol), 8-hydroxy quinoline (0.362 g, 0.0025 mol), Cul (0.476 g, 0.025 mol), irnidazole (1.36 g, 0.0199 mol), and potassium carbonate (2.52 g, 0.0183mol) in 17 mL of DMSO (degassed with argon for 10 mm) was heated at 120C under an atmosphere of argon for 15 h; the HPLC indicated no starting material. A 14% aqueous solution of ammonium hydroxide was added to the cooled mixture and this was stirred for I h at ambient temperature. Water (50 mL) and EtOAc (200 mL) were added and the aqueous layer was extracted with EtOAc (3x3OmL). The combined organic layers were dried over Na2SO4 andconcentrated, The crude product was purified by silica gel flash chromatography (eluted with EtOAc/hexanes) to provide 2.51 g of product.

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

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 24358-62-1, These common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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: (R)-1-(4-bromophenyl)ethanamine (2b) (2.00g, 10.0mmol) was dissolved in MeOH (50mL). To this solution was added 1-butanal (1.78mL, 20.0mmol) and NaBH(OAc)3 (4.24g, 20.0mmol). After stirring for 18h at room temperature, 5% NaOH was added. The mixture was extracted with CHCl3, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluted with 5-10% MeOH in CHCl3 to afford the titled compound (2.17g, 85%) as a colorless oil. 1H NMR (400MHz, CDCl3) delta: 7.44 (d, J=8.8Hz, 2H), 7.19 (d, J=8.8Hz, 2H), 3.72 (q, J=6.8Hz, 1H), 2.50-2.44 (m, 1H), 2.41-2.34 (m, 1H), 1.47-1.38 (m, 2H), 1.35-1.24 (m, 5H), 0.87 (t, J=7.3Hz, 3H). 13C NMR (100MHz, CDCl3) delta: 143.5, 131.6(2C), 128.5(2C), 120.8, 57.9, 47.2, 31.7, 23.7, 20.3, 13.9. LC-MS (ESI) m/z=256 [M+H]+.

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Imaizumi, Takamichi; Kobayashi, Atsuko; Otsubo, Shigeki; Komai, Masato; Magara, Megumiko; Otsubo, Nobumasa; Bioorganic and Medicinal Chemistry; vol. 27; 21; (2019);,
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. 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. COA of Formula: C8H8BrF

Step a. To a solution of 3-bromo-6-fluoro-o-xylene (CAS Number 52548-00-2; 3.00 g, 14.8 mmol) in CC1 (45 ml) was added NBS (5.780 g, 32.51 mmol) at rt. The reaction mixture was exposed to a UV light source which increased the temperature, in this manner the reaction mixture was heated at 85C for 2 h. The reaction mixture was cooled to rt and poured into saturated NaHC03 solution (100 ml). The resulting mixture was extracted with EtOAc (3 x 100 ml). The combined organic phase was washed with brine (100 ml), dried over Na2S04, filtered and concentrated under reduced pressure yielding 1-bromo-2,3-bis(bromomethyl)-4-fluorobenzene (5.80 g, 16.25 mmol). This material was directly used for next step without any further purification. LCMS: Method A, 2.489 min.

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

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); 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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H11Br

A solution of diethyl malonate (36.91 g, 230.4 mmol), anhydrous methanol (400 mL), and NaOMe (25% in methanol, 49.79 g, 230.4 mmol) is stirred at reflux for one hour under nitrogen. Bromomethyl-cyclopentane (31.31 g, 192.0 mmol) is added to the mixture, and stirred for an additional 3 hours. A solution of NaOH (23.04 g, 576.0 mmol) in water (400 mL) is added, and the mixture is stirred for an additional 1 hour at reflux. The mixture is cooled, diluted with water, and extracted with ether. The ether layer is discarded, and the aqueous layer is acidified with 1N HCl to pH=1. The aqueous layer is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. This gives 2-cyclopentylmethyl-malonic acid (21.0 g, 59% yield) as a white solid.

According to the analysis of related databases, 3814-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lee, Kwangho; Leeds, Jennifer A.; US2009/62537; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 134168-97-1,Some common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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 3-bromo-5-fluoroaniline (CAS 134168-97-1) (380 mg, 2.0 mmol) and 1-(2-chloroethyl)pyrrolidine (CAS 505041-9) (380 mg, 2.2 mmol) in NMP (20 mL) was heated to 120 C. overnight. The solution was diluted with EtOAc (100 mL) and washed with saturated Na2CO3 aqueous solution (3*40 mL). The combined organic layer were dried over Na2SO4, concentrated and purified by prep-TLC (DCM: MeOH=10:1) to give the titled product (290 mg, 50%). LCMS (0-60 AB), RT=1.076 min, M+H, 289.0

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

Reference:
Patent; Chen, Huifen; Crawford, Terry; Harris, Seth F.; Magnuson, Steven R.; Ndubaku, Chudi; Wang, Lan; US2013/324516; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 445-02-3, 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. 445-02-3 name is 4-Bromo-2-(trifluoromethyl)aniline, 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-Amino-5-bromobenzotrifluoride 9a (1.1 g, 4.58 mmol), 1,2,3-propanetriol (1.69 g, 18.3 mmol) and iron (II) sulfate heptahydrate (204 mg, 0.73 mmol) were added to a reaction flask. The reaction solution was cooled to 0C, and added dropwise with 0.8 mL of sulfuric acid. After completion of the addition, the reaction solution was heated to 120C, and stirred for 4 hours. The reaction was stopped, and the reaction solution was cooled to room temperature, added with 20 mL of water, and extracted with ethyl acetate (30 mL×3). The organic phases were combined, and concentrated under reduced pressure. The residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 9b (0.9 g), yield: 71.4%. MS m/z (ESI): 210.6 [M+1].

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

Reference:
Patent; Jiangsu Hengrui Medicine Co. Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; LU, Biao; ZHANG, Junzhen; JIN, Fangfang; HE, Feng; TAO, Weikang; EP3569596; (2019); A1;,
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 452-63-1 as follows. Recommanded Product: 452-63-1

A screw-capped vial (8 mL) was charged with compound 538 (100 mg, 0.37 MMOL) in 1,4-dioxane (2 mL), 2-bromo-5-fluoro-toluene (55 LULL, 0.44 MMOL), CS2C03 (169 mg, 0.52 MMOL), PD2 (dba) 3 (9 mg, 0.009 MMOL), and rac-BINAP (9 mg, 0.014 MMOL). The tube was capped with a rubber septum, flushed with argon for 5 min, and then stirred at 100 C for 18 h. The reaction mixture was allowed to cool to room temperature, and then poured into a mixture of water and EtOAc. The aqueous phase was extracted twice with more EtOAc. The combined organic phases were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The crude product was purified by chromatography eluting with EtOAc/petroleum ether 1: 3 to afford the title compound as light brown oil.

According to the analysis of related databases, 452-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 202865-83-6, These common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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.

Step 1: Preparation of 8-(3-fluoro-5-methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane A mixture of 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride (4.0 g, 22.3 mmol), 1-bromo- 3-fluoro-5-methylbenzene (5.05 g, 26.7 mmol), Pd2(dba)3 (408 mg, 445 mumol), Ruphos (416 mg, 891 mumol) and Cs2CO3 (18.1 g, 55.7 mmol) in toluene (50 mL) was heated with stirring at 120 C for 15 hrs. The resulting reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to give 8-(3-fluoro-5- methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (5.0g) as a yellow oil.

Statistics shows that 1-Bromo-3-fluoro-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 202865-83-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, belongs to bromides-buliding-blocks compound, 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 656-64-4, Application In Synthesis of 3-Bromo-4-fluoroaniline

General procedure: A stirred mixture of compound 5 (0.23 g, 0.001 mol), EDCI (0.23 g, 0.0012 mol), HOBt (0.16 g,0.0012 mol), aniline or aniline derivative (0.001 mol), and 20 mL DMF was reacted at room temperature overnight, and then 40 mL water was added and stirred for a quarter, before the crude was filtered and washed twice with water. The anticipated product was purified by column chromatography on silicagel using petroleum ether/ethyl acetate (2/1, volume ratio) as the eluent to afford the target compound.

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:
Article; Deng, Xinshan; Tan, Xiaoyu; An, Tiantian; Ma, Qingqing; Jin, Zhe; Wang, Ce; Meng, Qingguo; Hu, Chun; Molecules; vol. 24; 4; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary