3-(Trifluoromethyl)aniline → 3-(Trifluoromethyl)aniline

Participants

Reaction Conditions

Reaction Steps

Toluene (1,830 g) and m-trifluoromethylaniline (1,127 g; 7 moles) were introduced in an inert atmosphere into a 6 liter round flask. The reaction medium was stirred and heated to a temperature of 110° C. At that temperature, allyl chloride (382.5 g; 5 moles) and triethylamine (506 g; 5 moles) were added in parallel, over approximately 3 hours, with a lead of the order of 10% for allyl chloride. When the addition was complete, the reaction medium was maintained at a temperature of 115° C. for 1 hour and was then cooled to a temperature 30° C. The reaction mass was washed with water (4 washes with a total of 1.3 liter of water), to extract triethylamine hydrochloride. The organic phase was then distilled at atmospheric pressure and then under reduced pressure (<3,000 Pa). This resulted in the separation of toluene and unconverted m-trifluoromethylaniline (460 g; 2.86 moles) from N-allyl-m-trifluoromethylaniline (588 g; 2.92 moles), which corresponds to a 57% yield based on allyl chloride and 70% based on converted m-trifluoromethylaniline.

Provenance & Evidence