Acetic Acid → HCID 13929409, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromobenzotrifluoride (4.5 g, 20 mmol) and magnesium turnings (0.54 g, 22 mmol) were refluxed under a nitrogen atmosphere in 100 ml THF until the magnesium had dissolved. The resulting solution was cooled to -75° C. and added to 4.6 g (20 mmol) di-t-butyl azodicarboxylate in 100 ml THF at -75° C. The solution was warmed to -40° C., acetic acid (1.5 ml, 25 mmol) was added, and the mixture concentrated to 20 ml. Hexane and water were added, and the hexane solution was evaporated to leave a brown oil which was chromatographed on silica with 10% ether in CHCl3, providing 6.1 g (81% yield) of N,N'-bis(t-butoxycarbonyl)-2-(trifluoromethyl)phenylhydrazine as a brown gum. This material was dissolved in 200 ml isopropanol, and hydrogen chloride gas was passed into the solution resulting in a weight gain of 8 g. The solution was stirred at 50° C. for 30 minutes, then evaporated to dryness. The residue was treated with ether, and the solids collected by filtration and dried in vacuo, providing 2.7 g (79% yield) 2-(trifluoromethyl)phenylhydrazine hydrochloride as a white powder, mp 241°-242° C.

Provenance & Evidence