Bromocyclopentane → 4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

Participants

Reaction Conditions

Reaction Steps

To a solution 5-Bromo-2-methoxyphenol (30.6 g, 0.15 mmol) (preparation 3) in N, N-dimethylformamide (130 ml) under an argon atmosphere was added potassium carbonate (23.0 g, 0 . 17tool) and cyclopentyl bromide (18 ml, 0.18 mol). The resulting mixture was heated at 90° C. for 20 hr., at which time additional potassium carbonate (5.6 g, 0.04 mol) and cyclopentyl bromide (3 ml, 0.03 mmol) were added. Heating was resumed for 8 hr and additional potassium carbonate (5.6 g, 0.04 mol) and cyclopentyl bromide (3 ml, 0.03 mmol) were added. After heating at 90° C. for an additional 16 hr, the reaction mixture was allowed to cool and was concentrated under reduced pressure. The residue was partitioned between ether and water. The organic extract was washed with water (three times) and dried (magnesium sulfate). The solvate was removed in vacuo and the residue was purified by flash chromatography, eluting with 3% ether/hexanes to provide a pale yellow oil (29.8 g, 73%).

Provenance & Evidence