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

Participants

Reaction Steps

A solution of 5-bromo-2-methoxyphenol (74 g), cyclopentyl bromide (80.5 g) and potassium carbonate (73.6 g) in dimethylformamide (500 mL) is stirred at 60° C. for 16 hours. It is then concentrated and the resulting residue is treated with water (250 mL). This mixture is then extracted with dichloromethane (3×250 mL) and the combined extracts are dried over magnesium sulphate, and evaporated, to give 4-bromo-2-cyclopentyloxyanisole (95.5 g) in the form of a pale brown liquid. [NMR (CDCl3): 1.56-1.68 (m,2H), 1.77-1.99 (m,6H), 3.81 (s,3H), 4.71-4.75 (m,1H), 6.72 (d,1H), 6.98 (d,1H), 7.00 (dd,1H)].

Provenance & Evidence