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). While stirring under ice-cooling, a solution of N-bromosuccinimide (701.28 g, 3.94 mol) in acetonitrile (5 L) was added thereto dropwise. The temperature of the resultant mixture was raised to room temperature, and then the solvent was concentrated to about 3 L. n-Heptane (5 L) and water (5 L) were added thereto for extraction and liquid separation. The aqueous layer was further extracted with n-heptane (2 L) and separated into layers. The organic layer was mixed with the previously obtained organic layer, washed with aqueous solution of 5% sodium thiosulfate (1 L) and water (2 L), and concentrated under reduced pressure (35° C.) to give 977.0 g of the captioned compound as a slightly brown oily material (yield: 99.1%; HPLC purity: 95.8%).

Provenance & Evidence