Bromine → HCID 178517749, compound

Temperature

80 °C

To a solution of 5-(trifluoromethyl)pyridin-2-ol (10.52 g, 62 mmol) and sodium acetate (5.29 g, 64 mmol) in glacial acetic acid (38 mL) was added bromine (3.36 mL, 65 mmol) at room temperature. The white cloudy solution slowly turned into a clear brown solution, which was heated at 80° C. for 2.5 h. The mixture was allowed to cool to room temperature and then evaporated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution to pH=8. The resulting solution was extracted with EtOAc three times. The combined extracts were dried over MgSO4, filtered, and evaporated in vacuo to yield 15.1 g (99.8%) of the crude product (15.1 g, 98.8%) as a white solid. LC-MS calculated for C6H3BrF3NO: (M+H)+241.9; found 241.9/243.9.

1. temperatureto cool to room temperature
2. customevaporated under reduced pressure
3. extractionThe resulting solution was extracted with EtOAc three times
4. dry with materialThe combined extracts were dried over MgSO4
5. filtrationfiltered
6. customevaporated in vacuo

ORD record

ord-3c0d4368629748e4811a028d116aeb6d

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07307086B2