反应详情

温度

80 °C

A round-bottomed flask (50 cc) was charged with bis(5-amino-2-chloro-4-fluorophenyl)carbonate (1.50 g, 4.29 mmol), cyclopentyl methanesulfonate (1.50 g, 9.15 mmol) and tetrabutylammonium bromide (70 mg, 0.22 mmol) to prepare a solution in toluene (12 mL). Subsequently, 48% sodium hydroxide in aqueous solution (6 mL) was added slowly and the mixture was stirred under heating at 80° C. for 3 h. After completion of the reaction, the reaction mixture was cooled to room temperate and water (15 mL) was added, followed by extraction with toluene (10 mL×2). The organic layers were combined and washed with water (10 mL×2). The solvent was distilled off under vacuum from the resulting toluene solution, thereby giving 4-chloro-5-cyclopentyloxy-2-fluoroaniline (1.94 g, 8.45 mmol; yield=98.4%; purity on HPLC=94.3%). BP: 143°-145° C./1.5 mmHg 1H-NMR(CDCl3,TMS,ppm): δ1.40-2.00(8H,m), 3.72(2H,s), 4.76(1H,m), 6.39(1H,d,JHF =9.0Hz), 7.04(1H,d,JHF =11.0Hz). IR (neat, cm-1): 3500, 3400, 1630, 1510, 1420, 1245, 1185.

1. customAfter completion of the reaction
2. additionwas added
3. extractionfollowed by extraction with toluene (10 mL×2)
4. washwashed with water (10 mL×2)
5. distillationThe solvent was distilled off under vacuum from the resulting toluene solution