Sulfuric Acid → 2-Chloro-3-(trifluoromethyl)benzaldehyde

Participants

Reaction Steps

Butyl lithium (36.4 ml of 1.6M in hexane) was added to a stirred solution at -65° of 1-chloro-2-(trifluoromethyl)-benzene (10 g) in dry tetrahydrofuran (100 ml) over 20 mins. After stirring for 1.5 hours at -65°, a solution of N-methyl-N-phenylformamide (6.85 ml) in tetrahydrofuran (30 ml) was added over 1 hour. The reaction mixture was left at this temperature for 1.5 hours and then allowed to reach room temperature. It was then poured onto 10% sulphuric acid, extracted with ether and the organic extract was washed with brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was distilled (20 mmHg, oven temperature 100°-125°); the distillate was cooled, filtered and the solid washed with petroleum ether (60°-80°) to give the desired aldehyde (3.5 g) as a colourless solid.

Provenance & Evidence