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

Temperature

100 °C

NaOH (56.2 mL, 112 mmol) was added to a solution of 2-(4-bromo-2-fluorophenyl)acetonitrile (4.01 g, 18.74 mmol) in MeOH (30 mL). The mixture was stirred at 100° C. for 12 h. The mixture was cooled to rt. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(4-bromo-2-fluorophenyl)acetic acid (4.13 g, 17.72 mmol, 95.0% yield) was used to next step without further purification. TLC (PE/EA=1/1, Rf=0.4): 1H NMR (400 MHz, CDCl3) δ 7.22-7.31 (m, 2H), 7.13 (t, J=8.05 Hz, 1H), 3.67 (s, 2H); ES-LCMS m/z 232.9 (M+H).

1. temperatureThe mixture was cooled to rt
2. concentrationThen the solution was concentrated
3. extractionThe combined organic extract
4. washwas washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-3d0d42b611e848999b1922753356e0d8

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937071B2