Ethanol → Benzoic acid, 2-fluoro-5-(trifluoromethyl)-, ethyl ester

To a solution of 2-fluoro-5-(trifluoromethyl)benzoyl chloride (5.0 g, 22.0 mmol) in THF (25 mL) was added Et3N (3.1 mL, 22.0 mmol) followed by EtOH (1.3 mL, 22.0 mmol). This mixture was stirred at ambient temperature for 1 h and quenched with saturated, aqueous NH4Cl (10 mL). The layers were separated and the aqueous layer was extracted with 3×10 mL EtOAc and the combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc) to give the title compound (4.8 g, 20.3 mmol, 92% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.42 (t, J=7.1 Hz, 3 H), 4.43 (q, J=7.1 Hz, 2 H), 7.23-7.34 (m, 1 H), 7.74-7.82 (m, 1 H), 8.23 (dd, J=6.3, 2.4 Hz, 1 H).

1. customquenched with saturated, aqueous NH4Cl (10 mL)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with 3×10 mL EtOAc
4. dry with materialthe combined organics were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc)

ORD record

ord-6ad123aa98ca491fb1847e6548bd8c08

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835475B2