Dichloromethane → Tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate

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Reaction Steps

1-(Bromomethyl)-4-(trifluoromethoxy)benzene (1.23 mL, 7.7 mmol) and tetrabutylammonium hydrogen sulfate (2.85 g, 8.4 mmol) were added to a methylene chloride (50 mL) solution of tert-butyl [(diphenylmethylene)amino]acetate (compound described in J. Org. Chem., (1982), 47, 2663-2666, 2.07 g, 7.0 mmol) at room temperature according to the method described in the document (J. Org. Chem., (1995), 60, 601-607), and subsequently a 10% sodium hydroxide aqueous solution (21 mL) was added thereto. The mixture was vigorously stirred for 1.5 hours, and then to the reaction solution was added water. The resulting mixture was extracted with methylene chloride. The organic layer was collected, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (n-hexane to n-hexane:ethyl acetate, 19:1 and 9:1, V/V) twice to give 2.55 g of the title compound (white powder, yield: 78%).

Provenance & Evidence