Methanol → 2-(4-Bromo-2-fluorophenyl)acetic acid

Temperature

80 °C

To a solution of 2-(4-bromo-2-fluorophenyl)acetonitrile (397 g, 1.82 mol) in MeOH (500 mL) stirred under nitrogen at 20° C. was added NaOH (2.22 L, 2.5M, 5.56 mol) solution in one charge. The reaction mixture was stirred at 80° C. for 5 h. Then the solution was concentrated and neutralized with conc. HCl to pH=5 with stirring. Then the solution was extracted with EA (1.5 L×2). Another two batches were repeated using the same procedure. Then the three batches were combined. The combined organic extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the pure 2-(4-bromo-2-fluorophenyl)acetic acid (1200 g, 92% yield): TLC (PE/EA=5:1, Rf=0.2); 1H NMR (400 MHz, CDCl3) δ 7.24 (br. s., 1H), 7.12 (t, J=7.9 Hz, 1H), 3.65 (s, 2H).

1. additioncharge
2. concentrationThen the solution was concentrated
3. stirringwith stirring
4. extractionThen the solution was extracted with EA (1.5 L×2)
5. extractionThe combined organic extract
6. washwas washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-4d263a4ad2834bedb1cd8268de7e52c7

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2