Hydrochloric Acid → 2-(4-Bromo-2,6-difluorophenyl)acetic acid

Temperature

80 °C

A suspension of 2-(4-bromo-2,6-difluorophenyl)acetamide (7.20 mmol) in ethanol (10 mL) was treated with 6N aq sodium hydroxide (90 mmol) at room temperature. The vessel was then stirred in an oil bath at 80° C. After one hour the reaction mixture had turned clear. After stirring overnight, the reaction mixture was cooled to room temperature, at which point the pH was adjusted to ˜1 with 6N aq HCl. A white precipitate formed, and the solution was concentrated to a volume of ˜10 mL, at which point it was extracted three times with ethyl acetate. The combined organic layers were washed twice with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a solid (837 mg, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.60 (s, 2 H) 7.49 (d, J=6.82 Hz, 2 H) 12.82 (br. s., 1 H).

1. stirringAfter stirring overnight
2. temperaturethe reaction mixture was cooled to room temperature, at which point the pH
3. customA white precipitate formed
4. concentrationthe solution was concentrated to a volume of ˜10 mL, at which point it
5. extractionwas extracted three times with ethyl acetate
6. washThe combined organic layers were washed twice with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-dabb8ab7bacc4c2cbb17abcc8a52ec13

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09084794B2