3-(Trifluoromethyl)aniline → 3-iodo-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-iodo-4-methylbenzoic acid (3.00 g, 11.4 mmol) in DCM (30 mL) at 0° C. was added oxalyl chloride (1.45 mL, 17.2 mmol) followed by two drops of DMF. The reaction was stirred at 0° C. for 30 minutes followed by warming to ambient temperature for 40 minutes. The mixture was concentrated in vacuo. To the resulting residue was added DCM (30 mL), DIPEA (2.99 mL, 17.2 mmol) and 3-(trifluoromethyl)-benzenamine (1.42 mL, 11.4 mmol). The reaction was stirred at ambient temperature for 1 hour. The mixture was then poured into water, and the product was extracted with DCM. The combined organic extracts were washed with water, followed by saturated sodium bicarbonate, and then dried over sodium sulfate. An equal volume of hexane was added and most of the DCM was then removed in vacuo. The resulting yellow solid was filtered, rinsed with hexane and air dried. (4.27 g, 92%).

Provenance & Evidence