Isopropanol → 2-Iodo-5-(trifluoromethyl)benzoic acid

Potassium hydroxide (3.78 g; 0.0673 mol) was added to a stirred solution of 2-iodo-5-(trifluoromethyl)benzonitrile (Intermediate 8; 4 g; 0.0135 mol) in a 1:1 isopropanol:H2O solution (60 mL). The reaction was heated at reflux for 14 h and then partitioned between H2O (50 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL) and acidified to pH 5 with 6N HCl. The aqueous layer was further extracted with EtOAc (4×50 mL) and the combined extracts were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 2-iodo-5-(trifluoromethyl)benzoic acid as a yellow solid. LCMS=317.0 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 8.27 (d, J=1.6 Hz, 1H), 8.25 (d, J=8.2 Hz, 1H), 7.47 (dd, J=8.2, 1.8 Hz, 1H).

1. temperatureThe reaction was heated
2. temperatureat reflux for 14 h
3. custompartitioned between H2O (50 mL) and EtOAc (50 mL)
4. extractionThe aqueous layer was extracted with EtOAc (50 mL)
5. extractionThe aqueous layer was further extracted with EtOAc (4×50 mL)
6. washthe combined extracts were washed with brine (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-71d43a16453b47b1a08f33e0f7fa41c7

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865707B2