Dimethylformamide → HCID 54000509, compound

Temperature

10 °C

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).

1. temperatureThis solution is heated to 70° C. for 18 h
2. temperaturecooled
3. additionpoured into ice
4. stirringAfter stirring for 1 h
5. extractionthe mixture is extracted twice with diethyl ether (100 mL)
6. washthe ether extracts are washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customevaporated

ORD record

ord-8332ec39dc94403d817b614ec62ecc90

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051342B2