Sodium hydride → 4-Bromo-2-trifluoromethoxy-1-trifluoromethylthiobenzene

Temperature

23 °C

To a stirred solution of 4-bromo-2-trifluoromethoxybenzenethiol (1.76 g, 6.44 mmol) in DMF (10 mL) at 0° C. was added NaH (60% in mineral oil, 283 mg, 7.08 mmol) in small portions and the reaction mixture was slowly warmed to 23° C. over 30 minutes. The reaction vessel was evacuated and flushed with trifluoromethyl iodide gas and finally a balloon of trifluoromethyl iodide gas was attached and continued the reaction at 23° C. till the gas is consumed. The reaction mixture was heated to 80° C. with stirring for 2 h, cooled to room temperature and stirred overnight. The reaction mixture was poured into 1.0 N HCl (100 mL) and extracted with ethyl ether. The combined organic layer was washed with brine (80 mL), dried MgSO4 and concentrated in vacuo to get the crude product. This was purified by silica gel column chromatography using pentane as a eluent to afford 4-bromo-2-trifluoromethoxy-1-trifluoromethylthiobenzene (1.12 g, 51%).

1. customThe reaction vessel was evacuated
2. customflushed with trifluoromethyl iodide gas
3. customthe reaction at 23° C. till the gas
4. customis consumed
5. temperatureThe reaction mixture was heated to 80° C.
6. temperaturecooled to room temperature
7. stirringstirred overnight
8. additionThe reaction mixture was poured into 1.0 N HCl (100 mL)
9. extractionextracted with ethyl ether
10. washThe combined organic layer was washed with brine (80 mL), dried MgSO4
11. concentrationconcentrated in vacuo
12. customto get the crude product
13. customThis was purified by silica gel column chromatography

ORD record

ord-1f9664a1f2da41c5a681fb2f0416f235

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691843B2