Electric Literature of 74586-53-1,Some common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-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.
General procedure: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. Thetitle compound was prepared by reaction of 3-bromo-5-methylaniline (1000 mg, 5.38 mmol, 1 equiv) andcyclopropanesulfonyl chloride (1013 mg, 8.07 mmol, 1.5 equiv) according to MethodC. The product was purified by CC (hexane/ethyl acetate 8:2); yield: 77% (1200mg). 1H NMR (500 MHz, acetone-d6) delta 8.62 (br. s, 1H), 7.35 (s, 1H), 7.15(s, 1H), 7.13 (s, 1H), 2.65-2.61 (m, 1H), 2.30 (s, 3H), 1.00-0.95 (m, 4H).
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-5-methylaniline, its application will become more common.
Reference:
Article; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
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