Water → 6-Bromohexyl 4-(3-bromophenyl)butyl ether

Participants

Reaction Steps

A stirred mixture of 4-(3-bromophenyl)butan-1-ol (18 g) and 1,6 dibromohexane (48 ml) in 50% aq. sodium hydroxide (500 ml) with tetrabutylammonium bromide (1.5 g) was stirred for 2d at 20°. The mixture was poured into water (1000 ml) and extracted into ethyl acetate (3×500 ml). The combined extracts were washed with water (1000 ml), dried (Na2SO4). The solvent was removed in-vacuo and the residual oil was purified by flash chromatography (500 g) using dichloromethane as eluent, changing to light petroleum (40-60°)-diethyl ether (9:1) to give the title compound (18 g). LCMS RT=4.34 min.

Provenance & Evidence