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

Participants

Reaction Conditions

Reaction Steps

Sodium carbonate (318 g; 3 moles), water (0.5 liter), meta-trifluoromethylaniline (966 g; 6 moles) and triethylamine (20 g; 0.2 mole) were introduced, in an inert atmosphere, into a 2 liter round flask. The reaction medium was heated to a temperature of 50° C. with good stirring. Allyl chloride (230 g; 3 moles) was then introduced over approximately a 4 hour period. The temperature increased from 50° C. to 70° C. during the addition of allyl chloride. The reaction mass was then heated to a temperature of 100° C. for 1 hour before being cooled to about 50° C. After washing with water and phase separation, the organic phase was distilled under vacuum (5,000 Pa). This resulted in the separation of unconverted m-trifluoromethylaniline (540 g; 3.35 moles) from N-allyl-meta-trifluoromethylaniline (367 g; 1.83 moles), which corresponds to a 61% yield based on allyl chloride and a 70% yield based on meta-trifluoromethylaniline. The mass/volume output was 245 gel of reaction medium.

Provenance & Evidence