Chloromethyl Methyl Ether → 2-Bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene

Participants

Reaction Steps

To a stirring solution of 1-(2-bromo-4-methylphenyl)cyclopentanol (4.2 g, 16.5 mmol) in DCM (40 mL) at rt were successively added DIPEA (11 mL, 66 mmol) and MOMCl (2.5 mL, 33 mmol) over a 10 min period. The solution was stirred for 11 h at rt, and afterwards a NH4Cl-saturated aqueous solution (40 mL) was added. The aqueous phase was segregated, and the organic one was washed with water (30 mL), brine (30 mL), dried with anhydrous Na2SO4, filtered, and concentrated to give pure 2-bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene (4.0 g, yield 81%).

Provenance & Evidence