Chlorosuccinimide → tert-Butyl 1-(5-amino-2-chloro-4-fluorobenzyl)cyclopropanecarboxylate

Participants

Reaction Steps

2.0 g (7.54 mmol) of tert-butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate were dissolved in 20.0 ml of acetonitrile, and 1.06 g (7.92 mmol) of N-chlorosuccinimide were added in several portions at RT. The reaction mixture was stirred at RT for 80 min and then at 45° C. for 8 h. After cooling, the acetonitrile was removed under reduced pressure. The residue was taken up in dichloromethane and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. By chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1) 1.41 g (62.3% of theory) of the title compound were isolated from the crude product obtained in this manner.

Provenance & Evidence