Water → Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask (50 cc) was charged with bis(5-amino-2-chloro-4-fluorophenyl)carbonate (1.53 g, 4.39 mmol), propargyl bromide (1.11 g, 9.36 mmol) and tetrabutylammonium bromide (70 mg, 0.22 mmol) to prepare a solution in toluene (10 mL). Subsequently, 48% sodium hydroxide in aqueous solution (5 mL) was added slowly and the mixture was stirred under heating at 80° C. for 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature 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-2-fluoro-5-propargyloxyaniline (1.61 g, 8.08 mmol; yield=92.0%). 1H-NMR(CDCl3,TMS,ppm): δ2.54(1H,t,J=2.3Hz), 3.79(2H,brs), 4.70(2H,d,J=2.3Hz), 6.58(1H,d,JHF =8.9Hz), 7.07(1H,d,JHF =11.2Hz).

Provenance & Evidence