tert-Butanol → HCID 69992339, compound

Participants

Reaction Steps

N-Butyllithium (4.43 mL, 11.07 mmol) was added to a solution 2-methyl-2-propanol (1.0 mL, 10.53 mmol) in tetrahydrofuran (21 mL) at −10° C. under an argon atmosphere, and the mixture was stirred for 10 minutes. A solution of 4-(3-bromophenyl)butyric acid methyl ester (1.35 g, 5.27 mmol) in tetrahydrofuran (5.3 mL) was added dropwise at −10° C., and the mixture allowed to reach room temperature and stirred for 16 hours. Saturated ammonium chloride was added and the product extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (98:2), gave 4-(3-bromophenyl)butyric acid tert-butyl ester as a yellow oil (74%).

Provenance & Evidence