Category: 583-68-6

Related Products of 583-68-6, 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. 583-68-6 name is 2-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.

General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow.

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

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
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. 583-68-6, name is 2-Bromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 mol% of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 mol% of catalyst 5 was applied.

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 583-68-6.

Reference:
Article; Srinivas, Keesara; Saiprathima, Parvathaneni; Balaswamy, Kodicherla; Ra, Mandapati Mohan; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 162 – 167;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 583-68-6, 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. 583-68-6 name is 2-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.

General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow.

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

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 583-68-6,Some common heterocyclic compound, 583-68-6, name is 2-Bromo-4-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.

2-isocyano-5-methyl-biphenyl (1a):To a dry three necked flask, 2-bromo-4-methylaniline(S1,3.7 g, 20 mmol), phenylboronic acid (2.9 g, 24 mmol), aqueous solution of K2CO3 (2M, 15 mL) and DME (15 mL) were added,and the mixture was stirred for 30 min at room temperature under Ar atmosphere.To the stirred mixture, PdCl2 (PPh3)2 (280mg, 0.40 mmol) was added at room temperature, and the mixture was stirred for overnight at 80 C, under Ar. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and dried over anhydrous MgSO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography on silica gel(petroleum ether/EtOAc = 30/1) to afford 4-methyl-2-phenylaniline as yellow oil (S2, 3.2 g, 87%). Acetic formic anhydride, which was prepared from the reaction of acetic anhydride (1.3 mL) with formic acid (0.6 mL) at 55 C for 2 h, was added dropwise to a stirred solution of S2 (1.10 g, 6 mmol) at 0 C in THF (10 mL) and the mixture was stirred for 2 h at room temperature. Then, the mixture was quenched by sat.aqueous solution of NaHCO3 and extracted with EtOAc three times. The extract was dried over Na2SO4 and concentrated under reduced pressure to give formamide S3 as pale yellow oil. This material was used for the subsequent dehydration without further purification. THF (10 mL), NEt3 (6 mL) and the whole amount of S3 obtained above were added and cooled to 0 C.Then, POCl3 (0.9 mL, 10 mmol) was added dropwise, and the mixture was stirred at 0 C for 2 h. After the reaction was completed, the mixture was quenched by sat. aqueous solution of Na2CO3 and stirred for 1 h. The mixture was extracted with CHCl3 three times, dried over MgSO4 and evaporated under reduced pressure. The compound was purified by column chromatography on Florisil (hexane/EtOAc = 20/1) to give 1a as a white solid (0.89 g, 77% yield from S2).

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-4-methylaniline, its application will become more common.

Reference:
Article; Wang, Gao; Chen, Shan-Yong; Yu, Xiao-Qi; Tetrahedron Letters; vol. 55; 38; (2014); p. 5338 – 5341;,
Bromide – Wikipedia,
bromide – Wiktionary