Bromine → 4-Bromo-2-[(trifluoromethyl)sulfanyl]phenol

Temperature

-78 °C

To a stirred solution of 1-hydroxy-2-trifluoromethylthiobenzene (16 mmol, 1.0 eq.) in CH2Cl2 (40 mL) at −78° C. was added a solution of Br2 (0.83 mL, 16 mmol, 1.0 eq.) in CH2Cl2 (18 mL) slowly. The resulting mixture was stirred at −78° C. for 2 h and then warmed to room temperature overnight. The reaction mixture was diluted with water (300 mL) and extracted with CH2Cl2 (3×150 mL). The combined organic layer was washed with brine (400 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography using 0-10% EtOAc in hexanes as an eluent to afford 4-bromo-1-hydroxy-2-trifluoromethylthiobenzene in 93% yield as a crystalline solid.

1. temperaturewarmed to room temperature overnight
2. extractionextracted with CH2Cl2 (3×150 mL)
3. washThe combined organic layer was washed with brine (400 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe crude product was purified by column chromatography

ORD record

ord-ffeb37b852f64469997f16b077af38bf

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691843B2