Sodium hydride → 1-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-3-(trifluoromethyl)benzyl alcohol (2.87 g, 13.63 mmol) in DMF (40 mL) is added sodium hydride (60% in mineral oil, 654 mg, 16.36 mmol) at 0° C. and the reaction mixture is stirred at 0° C. for 30 minutes. 4-methoxy-benzyl chloride (2.35 g, 15 mmol) in DMF (10 mL) is added and the reaction mixture is stirred at 0° C. for 1 h and at room temperature for 3 hours. The reaction mixture is poured into saturated aqueous NH4Cl (300 mL) and extracted with EtOAc. The combined extracts are washed with brine (2×80 mL) and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (8:1 hexanes/EtOAc) to give 1-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene.

Provenance & Evidence