Triethylamine → HCID 86699739, compound

Participants

Reaction Steps

To a stirred solution of 4-bromo-2-methoxy-6-methyl-benzoic acid (synthesized according to the methods described in sections a) to d) of example 10) (2.0 g, 8.16 mmol) in dichloromethane (50 ml) are added oxalyl chloride (0.84 ml, 9.79 mmol) and dimethylformamide (catalytic amount) at 0° C. The reaction mixture is stirred for 30 min at RT. Excess oxalyl chloride is distilled off under nitrogen. The residue is dissolved in dichloromethane (20 ml), cooled to 0° C. followed by the addition of triethylamine (2.8 ml, 20.4 mmol) and 4-fluorobenzylamine (1.12 ml, 9.79 mmol). The reaction mixture is stirred for 1 h at RT. After completion of the reaction (monitored by TLC) the mixture is diluted with water (50 ml) and extracted with dichloromethane (3×50 ml). The organic layer is washed with water (50 ml), brine (50 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 15% ethyl acetate/hexane) to yield 4-bromo-N-[(4-fluorophenyl)-methyl]-2-methoxy-6-methyl-benzamide (2.70 g, 7.67 mmol, 94%).

Provenance & Evidence