Month: March 2021

These common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, 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. Computed Properties of C9H12BrN

A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g; 5.14 mmol), ethyl acrylate (0.8 ml; 7.70 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10.0 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg; 3.43 mmol).

The synthetic route of 1-(3-Bromophenyl)-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; EP1598353; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4263-52-9, 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. 4263-52-9, name is Sodium 2-bromoethanesulphonate belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 1-(2,2-diferrocenylpropane) methyl-imidazole (1.68g, 3.42mmol) and sodium 2-bromoethanesulphonate (0.72g, 3.42mmol) were refluxed at 80C for 16h in DMF (50mL). After cooling to room temperature, the reaction mixture was washed with H2O, and partitioned between H2O and CH2Cl2. The combined organic extract was dried (MgSO4) and concentrated. The residue was purified by silica gel (100-200mesh) chromatography to yield 2 (0.68g, 28%) as an orange-yellow solid. M.p. 46-47C. 1H NMR (400MHz, CDCl3): delta 9.22 (d, 1H, J=28.4Hz, NCHN), 7.50 (d, 1H, J=14.4Hz, NCH), 7.07 (d, 1H, J=7.6Hz, NCH), 5.10 (d, 2H, J=60.4Hz, CH2), 4.59 (s, 2H, CH2), 4.35-3.97 (m, 17H, Cp-H), 3.33 (s, 2H, CH2), 1.66-1.42 (m, 6H, CH3). 13C NMR (101MHz, CDCl3): delta 136.53 (N=C), 122.84 (N=C), 120.82 (N=C), 103.35 (N-CH2-Cp), 102.71 (N-CH2), 78.65 (Cp), 78.38 (Cp), 69.75 (Cp), 69.02 (Cp), 68.18 (Cp), 66,94 (Cp), 50.68 (Cp), 49.78 (Cp), 46.62 (CH2), 33.11 (CH3), 30.50 (CH3). MS (ESI) m/z 701.75 [M]+, 622.83 [M-Br]+, 599.08 [M-Br-Na]+, 78.83 [Br]- Cal. 702. IR (KBr cm-1): upsilon 3094 (=C-H), 2973 (C-H), 1640 (C=C), 1562 (C=N), 1447 (S=O), 1357, 1201, 1106, 1042, 1001, 817, 739, 479. HRMS (M-Br-Na)+: calcd 600.0828, obsd 600.0822.

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, Sodium 2-bromoethanesulphonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Su, Zhi-Ming; Ye, Hong-Min; Zhu, Xiao-Xiao; Xie, Li-Li; Bai, Sha; Yuan, Yao-Feng; Journal of Organometallic Chemistry; vol. 750; (2014); p. 162 – 168;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 314084-61-2,Some common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, molecular formula is C11H15Br, 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 a nitrogen atmosphere, 14.2 g of malonic acid dinitrile are added at normal pressure and room temperature to a mixture of 48 g of a 50% aqueous solution of sodium hydroxide and 300 g of 1-methyl-2-pyrrolidone. The reaction mixture is heated to from 60 to 100C, and 98 g of diluent are distilled off under reduced pressure (from 25 to 30 mbar). Under a nitrogen atmosphere, 45.5 g of 2-bromo-1, 3-diethyl-5-methylbenzene are added at normal pressure. The reaction mixture is then heated to 130C with stirring. At that temperature, a mixture of 0.26 g of TRIPHENYLPHOSPHINE, 0.2 g of a commercially available palladium (lI) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g of Pd (LI) chloride and 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-methyl-2-pyrrolidone is added. The mixture is stirred at from 125 to 130C for a further 3 hours and then 199 g of diluent are distilled off at reduced pressure (from 20 to 25 mbar) at from 90 to 100C. After cooling to room temperature, the reaction mixture is added to 126 g of water. 4.5 g of Hyflo (Celite) are added thereto, and the mixture is stirred for 30 minutes at 40C before being filtered. The filter cake is washed with 114 g of water. Following the addition of 45 g of 32% hydrochloric acid to the filtrate (a pH value of less than 5 is then established), the precipitated solid is filtered off and washed with 120 g of water. After drying, 42.8 G (content 97.3%, yield 98.0%) of 2- (2, 6-diethyl-4- METHYLPHENYL) MALONIC acid dinitrile having a melting point of from 79 to 82C are obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3-diethyl-5-methylbenzene, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 52723-82-7, 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 52723-82-7 as follows.

Example 47 4-Amino-2-fluoro-5-methylbenzonitrile Using the method of Example 15, 4-bromo-3-fluoro-6-methylaniline is converted into the title compound.

According to the analysis of related databases, 52723-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMERICAN CYANAMID COMPANY; EP224001; (1991); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-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.

To a solution of 3-bromo-4-fluorophenylamine (synthesised as described in J. Org. Chem. 1981, 46, 2280-2286) (415 mg, 2.18 mmol), cyclopropyl boronic acid (244 mg, 2.84 mmol), potassium phosphate (1.62 g, 7.64 mmol), and tricyclohexyl phosphine (61 mg, 0.22 mmol) in toluene (10 ml) and water (0.5 ml) was added palladium acetate (25 mg, 0.11 mmol) and the reaction mixture was heated to 100 C. overnight. The mixture was then cooled to RT and diluted with water and extracted with ether. The organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 3-cyclopropyl-4-fluorophenylamine (210 mg, 64%). MS (ISP) 152.2 (M+H)+.

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, Computed Properties of C7H8BrN

Take compound 1-1 (1.86g, 10mmol), compound 2-1 (3.17g, 12mmol), Pd (dppf) Cl2 (5mmol%), potassium carbonate (2.76g, 20mmol),50 mL of a mixed solvent of 1,4-dioxane and water (volume ratio 4:1) was added, and the reaction was performed at 100C for 6 hours after replacement with N2.The reaction was monitored by TLC. After the reaction was completed, the reaction solution was distilled off under reduced pressure.The residue was dissolved in a mixed solvent of methylene chloride and methanol, and filtered through celite,After the filtrate was concentrated, column chromatography (PE:EA=2:1) gave intermediate I-1 (light yellow solid, 73%),

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan University; Ye Tinghong; Wei Yuquan; Liu Zhihao; Wei Wei; Yu Luoting; (54 pag.)CN111205227; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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 a nitrogen atmosphere,In a 5 mL reaction tube with a Teflon magnetic stir bar,Add 0.015 mmol of cuprous iodide, 0.0075 mmol of 4,4′-di-tert-butyl-2,2′-bipyridine,6.0 mmol of tetrahydrofuran, 3.9 mmol of n-hexane,0.30 mmol 2-chlorophenylacetylene, 0.36 mmol (2-azidoethyl)benzene,0.39 mmol of pentafluoropropionic anhydride, and finally 0.45 mmol of triethylamine,Stir the reaction in a closed system for 15 h at 40 C in an oil bath and then cool to room temperature.Using trifluoromethoxybenzene as an internal standard, the 19F yield was greater than 99%.The organic phases were combined, filtered through 100-200 mesh silica gel and rinsed with dichloromethane.The organic solvent was removed by rotary evaporation to give a crude material.Eluted with n-pentane and dichloromethane (1:1, v/v),6-(2-Chlorophenyl)-3-(pentafluoroethyl)-4-phenylethyl-1,2,4-triazin-5(4H)-one (yield 99%) was obtained.

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

Reference:
Patent; Fuzhou University; Weng Zhiqiang; Wu Wei; (22 pag.)CN109111406; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 54962-75-3, 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

3-Bromo-5-(trifluoromethyl)aniline (20 g, 83 mmol) in acetic acid (150 ml) was treated portionwise with N-iodosuccinimide (20.62 g, 92 mmol). The reaction was stirred 24 h at ambient temperature. The reaction was diluted with ethyl acetate (600 mL) and was washed with aqueous sodium bisulfie (100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and evaporated. The residue was purified on a silica gel column with a gradient of ethyl acetate/hexanes from 7% to 15% to give 23.5 g (77%) of slightly impure product. 1H-NMR (CDCl3, 400 MHz) delta 7.21 (d, J=1.3 Hz, 1H), 6.82 (d, J=1.5 Hz, 1H), 4.57 (bs, 2H); LC/MS (HPLC method 4): tR=3.578 min, 365.80(MH)+.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18132; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

102169-44-8, name is 4-Bromo-5-methylbenzene-1,2-diamine, 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. Quality Control of 4-Bromo-5-methylbenzene-1,2-diamine

A mixture of (rac)-1-{[2,2-difluorocyclopropyl]methyl}-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and (1 .50 g), 4-bromo-5-fluorobenzene-1,2-diamine (833 mg), bis(triphenylphosphine)palladium(ll)chloride (143 mg), triphenylphosphine (53 mg) and potassium carbonate solution (2 M in water, 6.1 mL) were dissolved in 39 mL 1-propanol. This mixture was stirred at 120 C for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and dichloromethane/lsopropanol (7:3). The layers were separated and the aqueous layer was extracted with dichloromethane/lsopropanol twice. The combined organic layers were concentrated under reduced pressure. The crude product was purified by flash chromatography to provide the target compound: 850 mg, 85% purity. LC-MS (Method 2): Rt = 0.87 min; MS (ESIpos): m/z = 283 [M+H]+ 1H-NMR (400MHz, DMSO-d6): _ [ppm]= 1 .42 – 1 .57 (m, 1H), 1 .60 – 1 .78 (m, 1H), 2.14 – 2.31 (m, 1H), 4.24 (br d, 2H), 4.28 – 4.45 (m, 2H), 4.79 (s, 2H), 6.36 (d, 1H), 6.71 (d, 1H), 7.59 -7.68 (m, 1H), 7.86 (d, 1H).

The synthetic route of 102169-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LEFRANC, Julien; MENGEL, Anne; SCHULZE, Volker; CHRIST, Clara; PRINZ, Florian; WENGNER, Antje, Margret; STOeCKIGT, Detlef; BOeMER, Ulf; BADER, Benjamin; (288 pag.)WO2017/207534; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-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.

The starting material, 3,5-dibromoaniline(125.35 g, 499.6 mmol) to a round bottom flask in CH2Cl2 (2498ml) todissolve after, acetic anhydride (56.10 g, 549.5 mmol) and K2CO3 (82.85 g,599.5 mmol) at room temperature and the mixture It was stirred. Aftercompletion of reaction, then extracted with water and CH2Cl2 and the organiclayer the product was dried with MgSO4 and concentrated to 140.50 g wasobtained (96% yield).

The synthetic route of 626-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DuksanNeoluxCo., Ltd.; Oh, Dae Hwan; Kim, Dae Sung; Lee, Yun Suk; Jo, Hay Min; Jung, Yeong Suk; Choe, Yeon Hee; Kim, Suk Hyun; (69 pag.)KR101535606; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary