1,4-Dibromobenzene → HCID 18669677, compound

Participants

Reaction Steps

To a solution of 1,4-dibromobenzene (25.72 g, 109 mmol) in dry tetrahydrofuran (50 ml) at isopropanolg/dry ice bath temperature under argon was added n-butyl lithium (43.6 ml of 2.5 M solution in hexane, 109 mmol) dropwise. This was stirred for one hour during which time a slurry formed. This slurry was added via cannula to a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (20.0 g, 90.8 mmol) in dry THF (140 ml) at isopropanol/dry ice bath temperature. After one hour, the reaction was allowed to gradually warm to room temperature and stirred for an additional 4 h. The reaction was quenched with water then extracted three times with diethyl ether. The combined organic extract was washed successively with 1% hydrochloric acid, water, brine, then dried and evaporated. Purification by flash chromatography (silica gel, 17% ethyl acetate/83% hexane) provided the title compound as a pale white solid (36.78 g, 100% crude yield). MS (m/e): 359 [(M+1H2O)+]

Provenance & Evidence