Sodium hydride → 2-Bromo-4-chloro-1-(2,2,2-trifluoroethoxy)-benzene

To a stirred cold (0° C.) suspension of oil free NaH (0.12 mol, 4.8 g of 60% NaH in mineral oil) in anhydrous DMF (50 mL), a solution of 2-bromo-4-chlorophenol in DMF (50 mL) was added over 30 minutes under nitrogen. The resultant gray suspension of the sodium salt of 2-bromo-4-chlorophenol was treated with neat 2,2,2-trifluoroethylmethane sulfonate (21.4 g, 0.12 mol). The stirred mixture was heated at reflux temperature for 2-3 days. The mixture was cooled in an ice water bath and extracted with diethyl ether (2×100 mL). The combined ether extract was washed with 1N NaOH (3×100 mL), 1N HCl, brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to provide a golden-yellow oil (18.4 g) which was then distilled in vacuo to afford the title compound as a colorless oil (14.7 g): bp 100-103° C. @ 0.5 torr.

1. temperatureThe stirred mixture was heated
2. temperatureat reflux temperature for 2-3 days
3. temperatureThe mixture was cooled in an ice water bath
4. extractionextracted with diethyl ether (2×100 mL)
5. extractionThe combined ether extract
6. washwas washed with 1N NaOH (3×100 mL), 1N HCl, brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-f36ed8275b294710889e54f9ea7c2f30

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06469042B1