Dichloromethane → 1-Bromo-4-(tert-butoxy)benzene

Participants

Reaction Conditions

Reaction Steps

4-Bromophenol(57.8 mmoles, 10.0 g) was added to a -30° C. solution of isobutylene (40 ml) and methylene chloride (50 ml) and then cooled to -78° C. Trifluoromethanesulfonic acid (4 mmoles, 0.35 ml) was added. The mixture was held at -78° C. for 4 hours and then allowed to warm to room temperature. Triethylamine (0.5 ml) was added; the solvent was removed. The residue was chromatographed over silica gel eluted with 1% ethyl acetate in hexane to yield 12.4 g. (MS)

Provenance & Evidence