4-Chloroaniline → 5-bromo-N-(4-chlorophenyl)-2-methoxybenzamide

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Reaction Conditions

Reaction Steps

5-Bromo-2-methoxybenzoic acid (20 g) obtained in step B and 0.34 mL of N,N-dimethylformamide were dissolved in 380 mL of dichloromrethane, and the solution was cooled to 0° C. This solution was stirred for 30 minutes at 0° C., with oxalyl chloride (11.3 mL) being added little by little thereto, and then the mixture was stirred for 3 hours at room temperature. The reaction mixture was distilled under reduced pressure and dried to obtain a light yellow solid. This solid was added, with the use of 120 mL of dichloromethane, to a solution of 11.1 g of 4-chloroaniline and 45 mL of N,N-diisopropylethylamine dissolved in 380 mL of dichloromethane. The mixture was stirred for 2 hours and a half at room temperature, and then 300 mL of water was added. The organic layer was separated, and the aqueous layer was extracted twice with 100 mL of dichloromethane. After the respective organic layers were combined, the combined organic layer was washed with 200 mL of a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and then washed with dichloromethane. The filtrate and the washings were combined, dichloromethane was distilled off under reduced pressure, and the resulting residue was washed with methanol. The resulting solid was dried under reduced -pressure to obtain 23.6 g (80%) of 5-bromo-N-(4-chlorophenyl)-2-methoxybenzamide.

Provenance & Evidence