Allyl Alcohol → Tert-butyl (2-chloro-5-cyano-3-(3-oxopropyl)phenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate (500 mg, 1.508 mmol), 2-(di-t-butylphosphino)-2′-methylbiphenyl (14.13 mg, 0.045 mmol), and Pd2(dba)3 (13.81 mg, 0.015 mmol) were combined in a 40 dram vial which was evacuated and backfilled 3× with N2. To this was added acetonitrile (3 mL), N,N-dicyclohexylmethylamine (0.388 mL, 1.809 mmol), and prop-2-en-1-ol (0.154 mL, 2.262 mmol). The vial was again evacuated and backfilled with N2 3×, and heated at 90° C. for 3 h. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The material was purified by flash column chromatography (0%-50% EtOAc/Hex; 80 g column). Tert-butyl (2-chloro-5-cyano-3-(3-oxopropyl)phenyl)carbamate (184 mg) was obtained as a yellow glass.

Provenance & Evidence