N-bromobutanimide → 1-(3-Bromo-5-tert-butyl-4-hydroxyphenyl)ethanone

Participants

Reaction Steps

1-(3-tert-Butyl-4-hydroxyphenyl)ethanone (690.9 g, 3.75 mol) was dissolved in acetonitrile (6.05 L), and a solution of N-bromosuccinimide (701.28 g, 3.94 mol) in acetonitrile (5 L) was added dropwise while stirring on ice. After heating to room temperature, the solvent was concentrated to approximately 3 L. For extraction, n-heptane (5 L) and water (5 L) were added, and the solution was separated. The aqueous layer was extracted further with n-heptane (2 L), and the solution was separated. The organic layers were combined, washed with 5% aqueous sodium thiosulfate (1 L) and water (2 L), and concentrated under reduced pressure (35° C.) to obtain 977.0 g of the subject compound as a brownish oily substance (yield: 99.1%, HPLC purity: 95.8%).

Provenance & Evidence