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

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Reaction Steps

To a solution of crude (4-chloro-3-trifluoromethyl-phenyl)-methanol in DMF (anhydrous, 40 mL) at 0° C. is added NaH (600 mg, 15 mmol). After stirring for 30 min, 4-methoxy benzylbromide (2.21 g, 11 mmol) is added dropwise via syringe. After stirring at room temperature for 3 h, the reaction is quenched by pouring into a mixture of ice and saturated aqueous NH4Cl. The mixture is extracted with EtOAc (3×30 mL), and the combined organic layers are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the crude product is purified by silica gel chromatography (5% EtOAc in hexanes) to give 1-chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene as a colorless oil.

Provenance & Evidence