Water → 2-Bromo-6,7-dichloro-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenol

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Reaction Steps

6,7-Dichloro-1-(4-chlorophenyl)-3,4-dihydronaphthalene (3.0 g.) was dissolved in acetone (80 ml.), then water (30 ml.) was added, followed by a solution of N-bromoacetamide (3.0 g.) in acetone (40 ml.), and the mixture was stirred for 2 hours. The reaction mixture was then poured into water (150 ml.) and extracted with ether (3×80 ml.), the extracts were combined and dried, and the solvent was evaporated under reduced pressure to leave an oil. This residual oil was chromatographed on silica (Merck's Grade 7734), using 30% by volume of diethyl ether in petroleum ether (b.p. 60°-80° C.) as the eluant, to give the required 2-bromo-6,7-dichloro-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthol, m.p. 103°-104.5° C.

Provenance & Evidence