Hydrochloric Acid → 4-[1-(3-Bromo-phenyl)-vinyl]-phenol

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium (1.6 M solution in hexane, 41.6 mL, 1.1 eq) was added dropwise to a solution of 1,3-dibromobenzene (7.6 mL, 1.1 eq) in tetrahydrofuran (30 mL) at −78° C. After stirring 30 min at −78° C. 1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone (12.6 g, 57 mmol, 1 eq) in tetrahydrofuran (25 mL) was added dropwise. The mixture was allowed to warm up to room temperature and stirred for 2 h, then treated with 1 N HCl (10 mL), extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo. The crude was dissolved in toluene (40 mL) and p-toluenesulfonic acid (50 mg) was added. The mixture was heated at 150° C. for 3 h. The solvent was removed under reduce pressure and the residue was purified by column chromatography (cyclohexane) to afford the title compound as a colorless oil (1.2 g, 10%);

Provenance & Evidence