Methyl chloroformate → HCID 15614951, compound

Participants

Reaction Steps

2-Bromo-6-methoxy-5-(trifluoromethyl)-1-naphthalenecarboxamide (4.18 g, 12.01 mmol) was added to a stirred suspension of sodium hydride (50% dispersion in mineral oil, 632 mg, 1.1 eq) in anhydrous THF (110 mL) precooled in an ice bath under a dry N2 atmosphere. The ice bath was removed and the suspension was stirred at ambient temperature for 30 minutes, warmed to 40° C. and stirred an additional 20 minutes. The reaction mixture was cooled to room temperature and methyl chloroformate (0.93 mL, 1.0 eq) in THF (25 mL) was added dropwise over a 10 minute period. After an additional 20 minutes, saturated aqueous NH4Cl (35 mL) was added. The reaction mixture was added to water (400 mL) and extracted with ether (2×300 mL). The combined ether extracts were washed with saturated aqueous NaCl (300 mL). Silica gel (25 mL) was added to the ether solution and the solvent was removed. The silica absorbate was flash chromatographed (3:2 petroleum ether:ethyl acetate, silica) to provide the title compound as a white solid (2.71 g, 56%) m.p. 180°-182° C.

Provenance & Evidence