Hydrogen Bromide → Ethyl 2-bromo-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoate

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Reaction Steps

5-Amino-2-methoxy-N-[[4-(trifluoromethyl)phenyl]-methyl]benzamide (7.00 g, 21.6 mmol), 85 ml of acetone and 34 ml of methanol were mixed, which was cooled with ice. Under stirring, 17.5 ml of 47% hydrobromic acid, sodium nitrite (1.65 g, 23.9 mmol) and 6.2 ml of water were added and the mixture was stirred for 10 minutes. Next, ethyl acrylate (13.4 ml, 128 mmol) and copper oxide (I) (416 mg, 2.91 mmol) were added at room temperature. After stirring for 30 minutes, the reaction mixture was poured into saturated aqueous solution of sodium hydrogencarbonate, which was extracted with ethyl acetate. The extract was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from a mixed solvent of n-hexane with ethyl acetate to obtain 683 mg (71%) of the title compound as colorless crystals.

Provenance & Evidence