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

To a stirred solution of 2-bromo-4-chlorophenol (3.38 g, 16.3 mmol) in anhydrous 1-methyl-2-pyrrolidinone (25 ml) under an atmosphere of nitrogen, was added cesium carbonate (8.0 g, 24.4 mmol). The mixture was cooled to 0° C. before addition of 2,2,2-trifluoroethyl trifluoromethanesulfonate (3.78 g, 16.3 mmol) drop-wise over 2 minutes. The reaction was allowed to warm to room temperature and stirred for 14 hours. To encourage complete reaction the reaction mixture was warmed to 120° C. for 3 hours. The reaction mixture was cooled to room temperature then water (50 ml) was added. The layers were separated and the aqueous was extracted with heptane (3×50 ml). All organic extracts were combined then dried over anhydrous Na2SO4 (s), filtered and evaporated in vacuo to afford crude title compound as a yellow oil (4.20 g, 89%). Material was taken on without further purification.

1. customreaction the reaction mixture
2. temperaturewas warmed to 120° C. for 3 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. customThe layers were separated
5. extractionthe aqueous was extracted with heptane (3×50 ml)
6. dry with materialAll organic extracts were combined then dried over anhydrous Na2SO4 (s)
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-d667efc9166e4d5fb6749b78c341c0f2

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2