2-(4-Fluorophenyl)acetic acid → 2-(4-Fluorophenyl)acetamide

Temperature

0 °C

4-Fluorophenylacetic acid (1 g, 6.49 mmol) was dissolved in acetonitrile (40 ml) and cooled to 0° C. in an ice bath. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.492 g, 7.79 mmol) was added, followed by 1-hydroxybenzotriazole (1.19 g, 7.79 mmol). The mixture was stirred at 0° C. for 2.5 hours, and then concentrated ammonium hydroxide (0.865 ml, 13.0 mmol) was added slowly. The mixture then stirred at RT for an additional 2 hours. After this time the solids were filtered off, and the filtrate was diluted with ethyl acetate (50 mL). The solution was washed with saturated aqueous NaHCO3 (2×50 mL) and brine (50 mL), dried (MgSO4) and concentrated in vacuo to yield 2-(4-fluorophenyl)acetamide (0.87 g, 88% yield) as a white solid which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): δ 7.45 (broad s, 1H), 7.26 (m, 2H), 7.09 (m, 2H), 6.87 (broad s, 1H), 3.34 (s, H).

1. stirringThe mixture then stirred at RT for an additional 2 hours
2. filtrationAfter this time the solids were filtered off
3. additionthe filtrate was diluted with ethyl acetate (50 mL)
4. washThe solution was washed with saturated aqueous NaHCO3 (2×50 mL) and brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-165f83a4fe37433d9a136aa912aa87a6

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278331B2