2,2,2-Trifluoroethanol → HCID 949189, compound

2,2,2-Trifluoroethanol (0.35 mL, 4.80 mmol) was dissolved in THF (2 mL) and cooled to 0 C under nitrogen. Sodium hydride (60% dispersion in mineral oil, 0.192 g, 4.80 mmol) was added portionwise and the mixture stirred for 10 min. A solution of methyl 4-(bromomethyl)benzoate in THF (3 mL) was added, the mixture was warmed to room temperature and then heated to 50 C for 3 h. The mixture was then diluted with water (15 mL) and EtOAc (20 mL). The organic layer was separated and the aqueous neutralised with 1M hydrochloric acid. The aqueous layer was further extracted with EtOAc (2×20 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford the title compound as a colourless oily residue (1.05 g, 97%). 1H NMR (500 MHZ, CDCl3) δ ppm 7.95 (2H, d), 7.33 (2H, d), 4.64 (2H, s), 3.83 (3H, s) and 3.77 (2H, q).

1. temperaturecooled to 0 C under nitrogen
2. temperatureheated to 50 C for 3 h
3. customThe organic layer was separated
4. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated under vacuum

ORD record

ord-185c01df736e431080600c8f96df8a2c

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895733B2