Acetic Anhydride → HCID 54085736, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of acetic anhydride (60 mL), 4-(methylthio)benzaldehyde (4.99 g, 33 mmol), 3-fluorophenylacetic acid (5.08 g, 33 mmol), and triethylamine (3.98 g, 39 mmol) was heated to reflux for 4 hours. The reaction was cooled to 120° C., and water (120 mL) was added through an addition funnel. A yellow precipitate formed and, after further cooling to room temperature, was collected by filtration, washed with water, and recrystallized from toluene to give the desired intermediate as a yellow solid (3.72 g, 39%): mp 184°-187° C. 1H NMR (CDCl3) 300 MHz 7.92 (s,1H), 7.35 (m, 1H), 7.26 (d, J=6.3 Hz, 1H), 7.19 (d, J=7.7 Hz, 1H) 7.00 (m, 5H), 2.44 and 2.36 (s, 3H); 19F NMR (CDCl3) -112.61 (m). Mass spectrum M+H=289.

Provenance & Evidence