Dimethylformamide → HCID 54000509, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing phosphorus oxychloride (3.25 mL, 34.9 mmol) is cooled to ca. 10° C., and dimethylformamide (3.25 mL) is added dropwise. After stirring for 30 min, the resulting mixture is treated dropwise with a solution of 2-fluorophenylacetic acid (1.79 g, 11.6 mmol) in dimethylformamide (6 mL). This solution is heated to 70° C. for 18 h, then cooled and poured into ice. After being allowed to melt, the mixture is neutralized with solid NaHCO3, and then made basic with 50% aq. NaOH solution. After stirring for 1 h, the mixture is extracted twice with diethyl ether (100 mL), and the ether extracts are washed with brine, combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford 3-dimethylamino-2-(2-fluorophenyl)-acrolein (1.72 g, 8.92 mmol, 77%) as a yellow-brown oil. TLC RF 0.30 (ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 9.08 (1H, s), 7.29-7.19 (2H, m), 7.14-7.01 (2H, m), 6.91 (1H, s), 2.88 (6H, br). MS (ES+): m/e 216 (18), 195 (23), 194 (100).

Provenance & Evidence