3-Bromo-2-methylaniline

3-Bromo-2-methylaniline is a 3-halo-2-methylaniline derivative. 3-bromo-2-methylaniline is an important organic intermediate (building block) to synthetize substituted aniline products. 3-Bromo-2-methylaniline may be used in the preparation of 3,4-dibromo-2-methylaniline, racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Tröger’s base, 4-bromo-1H-indazole, and so on.

• 3,4-dibromo-2-methylaniline
• racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Trger′s base
• 4-bromo-1H-indazole

55289-35-5

55289-36-6

General procedure for the synthesis of 3-bromo-2-methylaniline from 2-bromo-6-nitrotoluene: 2-bromo-6-nitrotoluene (500 mg, 2.32 mmol) and stannous dichloride hydrate (2.62 g, 11.63 mmol) were dissolved in ethanol, and the reaction was stirred for 3 hours at 80°C. After completion of the reaction, ethanol was removed by rotary evaporation. Subsequently, the pH of the reaction mixture was adjusted with saturated aqueous sodium bicarbonate to about 8. The mixture was filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrates were combined and extracted three times with ethyl acetate. Finally, the combined organic phases were dried by rotary evaporation to give 3-bromo-2-methylaniline (410 mg, 2.20 mmol) in 95% yield.