反应详情

(I1C): DMF (2 mL) was cooled to −20° C. and treated gradually in dropwise manner with oxalyl chloride (0.216 mL, 2.469 mmol). After 10 min, a solution of 3-bromo-4-hydroxy-5-nitrobenzonitrile (200 mg, 0.823 mmol) in DMF (2 mL) was added slowly via syringe while maintaining internal temperature below −10° C. After addition, the mixture was allowed to warm to room temperature and then heated at 100° C. for 1.5 h. The reaction mixture was cooled and poured into ice-water; the solid was collected by filtration, rinsed with water and dried to give 172 mg of 3-bromo-4-chloro-5-nitrobenzonitrile as tan solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.13 (1H, d, J=1.76 Hz), 8.02 (1H, d, J=1.98 Hz)

1. temperaturewhile maintaining internal temperature below −10° C
2. additionAfter addition
3. temperatureheated at 100° C. for 1.5 h
4. temperatureThe reaction mixture was cooled
5. filtrationthe solid was collected by filtration
6. washrinsed with water
7. customdried