Reference of 583-75-5,Some common heterocyclic compound, 583-75-5, name is 4-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.
4-bromo-2-methylaniline (5.0 g, 27 mmol) was added to a mixture of water (12.3 ml) and HBF4 (48% by weight in water, 12.3 ml, 67 mmol) in a Nalger reaction vessel cooled in an ice water bath. Then, NaNO2 (1.85 g, 27 mmol) in water (3.8 ml) was added while maintaining the temperature of the reaction around 10 C. After 15 minutes, the was then recooled in an ice water bath and filtered via a Buchner funnel. The solid was washed with cold 5% aqueous HBF4, cold MeOH (20 ml) and diethyl ether (3 x 10 ml). The solid was dried on a Buchner funnel for 1 hour and then added to a flask containing KOAc (5.3 g, 54 mmol, dried in vacuo overnight) and 18-C-6 (0.35 g, 1,3 mmol) suspended in chloroform (250 ml). The reaction was stirred at room temperature for 2 hours and then filtered, and the solid was washed with chloroform. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, concentrated, and diluted with water (250 ml). The suspension was filtered, and the solid was washed with hexanes (50 ml) and diethyl ether (50 ml), collected, and dried in vacuo to give title compound (3.6 g, 68%). MS (ESI pos. ion) m/z: 197 (M+H). Calc’d Exact Mass for C7H5BrN2: 196.
The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary