Chloromethyl Methyl Ether → 1-(Methoxymethoxy)-2-(trifluoromethoxy)benzene

Participants

Reaction Steps

A solution of 2-(trifluoromethyloxy)phenol (12.0 g, 67.4 mmol) in dichloromethane (45 mL) was cooled to 5° C., and N,N-diisopropylethylamine (23.5 mL, 135 mmol) and methoxymethyl chloride (7.68 mL, 135 mmol) were added dropwise, keeping the internal temperature ≦15° C. The reaction mixture was warmed to ambient temperature, stirred for 15 min at ambient temperature, then diluted with MTBE (250 mL) and washed with 2N HCl (2×50 mL), water (50 mL), 2N NaOH (2×30 mL), water (30 mL), and brine (30 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give the title compound (13.9 g, 62.6 mmol, 93%) which was used without further purification. MS (DCI/NH3) m/z 222 (M+H)+.

Provenance & Evidence