Acetic Acid → 4-(2,4-Difluorophenyl)-1,1,1-trifluoro-4-hydroxy-3-buten-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 40.0 g (0.256 moles) 2',4'-difluoroacetophenone (commercially available) in 400 mL diethyl ether at 0° C. was added 40 mL (0.405 moles) ethyl trifluoroacetate. At 5° C., 80 mL of a 25% wt. sodium methoxide in methanol (0.37 moles) were added over 15 minutes. The reaction mixture was stirred overnight at 25° C. The mixture was poured over 300 mL ice water and 21.3 mL (0.37 moles) acetic acid were added. The organic layer was washed two times with water, dried over anhydrous MgSO4, and concentrated in vacuo to give 62.85 g (97%) 4-(2,4-difluorophenyl)-1,1,1-trifluoro-4-hydroxy-3-buten-2-one as a yellow oil; 1HNMR (CDCl3) ppm: 6.61 (s,1H), 6.87 (m,1H), 6.97 (m,1H), 7.97 (m,1H).

Provenance & Evidence