Diisopropylamine → 2-(2,4-Difluoroanilino)-4,5-difluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide was generated at −5° C. by combining diisopropylamine (7.2 mL, 51 mmol) and n-butyl lithium (33 mL, 53 mmol) in 150 mL of dry THF. After 30 minutes, the solution was cooled to −78° C. and 2,4-difluoroaniline (3.46 mL, 34 mmol) was added and stirred for 2 hours. 2,4,5-Trifluorobenzoic acid (3.0 g, 17 mmol) was added, and the mixture was allowed to warm to room temperature over 17 hours. A saturated solution of HCl/dioxane (10 mL) was added, and after 1 hour the mixture was concentrated to a solid. The solid was redissolved in chloroform and washed with 1N HCl, water, and brine. The solution was dried and concentrated to afford 4.54 g of the title compound as a solid.

Provenance & Evidence