Category: 55289-36-6

Synthetic Route of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 2-methylbiphenyl-3-amine A mixture of 3-bromo-2-methylaniline (Aldrich, cat#530018: 0.39 mL, 3.2 mmol), phenylboronic acid (Aldrich, cat#P20009: 0.50 g, 4.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Aldrich, cat#697230: 0.13 g, 0.16 mmol) and potassium carbonate (1.32 g, 9.57 mmol) in 1,4-dioxane (20.0 mL) and water (7 mL) was sparged with nitrogen for 5 min. The mixture was then heated and stirred at 110 C. for 1.5 h. The reaction mixture was cooled to room temperature, quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate (3*10 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexanes (0?15%) to afford the desired product. LC-MS calculated for C13H14N (M+H)+: m/z=184.1; found 184.1. 1H NMR (400 MHz, DMSO) delta 7.40 (dd, J=7.6, 6.8 Hz, 2H), 7.32 (dd, J=7.6, 7.2 Hz, 1H), 7.29-7.14 (m, 2H), 6.92 (dd, J=7.6, 7.6 Hz, 1H), 6.64 (d, J=7.2 Hz, 1H), 6.40 (d, J=7.2 Hz, 1H), 4.89 (s, 2H), 1.92 (s, 3H).

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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Lajkiewicz, Neil; Wu, Liangxing; Yao, Wenqing; (58 pag.)US2017/174679; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 55289-36-6, name is 3-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 55289-36-6, Recommanded Product: 55289-36-6

68A. 3-bromo-2-methylphenol To a solution of 3-bromo-2-methylaniline (6 g, 32.2 mmol) in sulfuric acid (38.7 mL, 38.7 mmol) at 0 C. was added slowly of a solution of sodium nitrite (2.67 g, 38.7 mmol). After stirring at 0 C. for 15 min, sulfuric acid (13.75 mL, 258 mmol) was added and the solution was heated at 100 C. for 1 h. The mixture was diluted with water, extracted with Et2O, dried and concentrated. Purification via silica gel chromatography gave 68A (light brown solid, 4.92 g, 82% yield).

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; Bristol-Myers Squibb Company; US2011/82165; (2011); 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 55289-36-6 as follows. Computed Properties of C7H8BrN

Reference Production Example 3 (0555) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanato-2-methylbenzene. 1-Bromo-3-isocyanato-2-methylbenzene (0556) (0557) 1H-NMR (CDCl3) delta (ppm): 7.39 (1H, dd, 1.5, 7.7 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.00 (1H, dt, J=0.5, 8.0 Hz), 2.42 (3H, s).

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; HOU, Zengye; TAKAHASHI, Teruki; (156 pag.)US2016/174558; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-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.

A solution of triphosgene (2.25 g, 7.58 mmol) in toluene (27 mL), cooled in an ice-water bath, was treated slowly with a solution of 3-bromo-2-methylaniline (3.00 g, 16.1 mmol) and DIEA (5.6 mL, 32.2 mmol) in toluene (5.4 mL). The resulting suspension was stirred at room temperature for 2 h. The precipitate was removed by filtration and washed with EtOAc. The combined filtrates were diluted with EtOAc, washed with brine, dried and concentrated to provide l-bromo-3-isocyanato-2- methylbenzene as a brown oil (3.68 g, 98%). NMR (400 MHz, DMSO-d6) delta 7.49 (dd, J=8.1, 0.9 Hz, 1H), 7.31 (dd, J=7.9, 0.7 Hz, 1H), 7.15 (td, J=8.0, 0.7 Hz, 1H), 2.38 (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 3-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-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. name: 3-Bromo-2-methylaniline

To a vigorously stirred solution of 3-bromo-2-methylaniline (5.0 g, 26.9 mmol) in a 1 :1 mixture of dichloromethane (67.2 mL) and sodium bicarbonate (80.6 mL, 1 .15 M) was added dropwise a solution of triphosgene (2.79 g, 9.41 mmol, 0.35 equiv) in (15 mL) at 0C. The reaction mixture was stirred until no more gas formation was observed. The organic and water phases were separated. The aqueous phase was extracted with dichloromethane, and the combined organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure to give 1-bromo-3- isocyanato-2-methyl-benzene (5.70 g, 98 %) as a brown liquid that was used in the next step without further purification. NMR (400 MHz, CDCIs) delta 7.40 (dd, J = 7.9, 1.5 Hz, 1 H), 7.05 (dd, J = 8.0, 1.5 Hz, 1 H), 7.00 (t, J = 7.9 Hz, 1 H), 2.43 (s, 3H). LC (method A): 0.99 min.

The synthetic route of 3-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; QUARANTA, Laura; BOU HAMDAN, Farhan; POULIOT, Martin; RENDINE, Stefano; (94 pag.)WO2018/114541; (2018); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromo-2-methyl-aniline (10 g, 53.75 mmol) and 4,4,5,5-tetramethyl-2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (27.30 g, 107.50 mmol) in dioxane (300 mL) were added KOAc (10.55 g, 107.50 mmol) and Pd(dppf)Cl2(3.93 g, 5.37 mmol) under N2.The mixture was stirred at 90 C for 12 h, and then concentrated. The residue was purified by flash silica gel chromatography (ISCO; 120 g SEP FLASH Silica Flash Column, Eluent of 0-15% Ethyl acetate/Petroleum ether gradient 100 mL/min) to give 2- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (8 g, 56.82% yield) as a yellow solid. LCMS: m/z found 234.2 [M+H]+.

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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; BI, Yingzhi; DORSEY, Bruce D.; FAN, Yi; MOORE, Christopher Brooks; NGUYEN, Duyan; (169 pag.)WO2019/191624; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-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. Computed Properties of C7H8BrN

A mixture of 1-bromo-2-methyl-3-aminobenzene 25.0 g, triphosgene 60.0 g and toluene 400 mL was stirred withheating under ref lux for three hours. The reaction mixtures after standing to cool were concentrated under reduced pressure to give l-bromo-3-isocyanato-2- methylbenzene 30.3 g.?H NMR (CDC13) : 2.42(3H, 5), 7.00(1H, dt, J=0.5, 8.0Hz), 7.05(1H, dd, J=1.7, 8.0Hz), 7.39(1H,dd, 1.5, 7.7Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55289-36-6, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; YOSHIMOTO, Yuya; TAKAHASHI, Teruki; OOHIRA, Daisuke; AZUMA, Shuhei; WO2013/162077; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-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.

Tetrakis(triphenylphosphine)palladium(0) (Aldrich, catNo.216666: 300 mg, 0.3 mmol) was added to a mixture of 3-bromo-2-methylaniline (Aldrich, catNo.530018: 1000 mg, 5 mmol), phenylboronic acid (Aldrich, catNo.P20009: 600 mg, 5 mmol), 1,4-dioxane (20 mL, 200 mmol) and water (3 mL, 200 mmol), and the mixture was allowed to stir at 100 C. overnight. After concentration, the residue was dissolved in DCM and washed with brine. The organic layer was dried and concentrated to afford desired product as a brown solid, which was used in the next step without further purification. LC-MS calculated for C13H14N (M+H)+: m/z=184.1; found 184.1.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Yu, Zhiyong; Wu, Liangxing; Yao, Wenqing; (44 pag.)US2018/16260; (2018); 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. 55289-36-6, name is 3-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

A mixture of sodium 2-(3-methoxypyridin-2-yl)acetate (0.166 g, 0.871 mmol), 3- bromo-2-methylaniline (0.1 18 mL, 0.958 mmol), DIEA (0.608 mL, 3.48 mmol) and HATU (0.397 g, 1.045 mmol) in DMF (4.0 mL) was stirred at room temperature. After 1 h, the mixture was diluted with EtOAc and washed twice with 10% aqueous LiCl, then with brine, dried and concentrated. The residue was purified by column chromatography on silica gel to provide N-(3-bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl) acetamide as a pale yellow solid (0.213 g, 73% yield). Mass spectrum m/z 335, 337 (M+H)+.

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 55289-36-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-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.

Acetic anhydride (2.27 eqiv) was added to a cooled 0 C solution of bromomethylaniline (1.00 eqiv) in chloroform (1.5 mL/mol) while maintaining the temperature below 40 C. The reaction mixture was allowed to warm to room temperature and was maintained for 1 h. Potassium acetate (0.29 eq) and isoamyl nitrite (2.15 eqiv) was added and the reaction mixture was heated at reflux for 18 h. The volatiles were removed under reduced pressure. Water (0.65 L/mol) was added to the residue and the mixture was concentrated. Concentrated hydrochloric acid (1 L/mol) was added to the residue and the mixture was heated at 50 C for 2 h. The mixture was allowed to cool to room temperature and the pH was adjusted to 10 by the slow addition of a 50% aqueous sodium hydroxide solution. The mixture was diluted with water (0.65 L/mol) and was extracted with ethyl acetate (2 x 1.2 L/mol). The combined extracts were washed with brine (1 L/mol) and dried over anhydrous sodium sulfate. The organic solution was filtered through a plug of silica gel (ethyl acetate wash), concentrated, and the residue was triturated with heptane (1 L/mol). The solids were collected by filtration, rinsed with heptane, and dried in a vacuum oven.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Memory Pharmaceuticals Corporation; WO2004/29050; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary