Cesium carbonate → 3-(Difluoromethoxy)bromobenzene

Temperature

100 °C

To a solution of 3-bromophenol (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (1.28 g, 7.39 mmol) in DMF (12.0 mL) was added sodium 2-chloro-2,2-difluoroacetate (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (2.82 g, 18.49 mmol) and Cs2CO3 (4.82 g, 14.79 mmol). The reaction mixture was heated at 100° C. Gas was released from the reaction so care should be taken. After 2 hours, the reaction was cooled to room temperature then diluted with EtOAc, washed with water and then brine and re-extracted three times with EtOAc. The combined organic layers were dried over magnesium sulfate and then filtered, concentrated, and purified with silica gel chromatography (0-5% EtOAc in hexanes) to yield T18.1 as an oil that was used without further purification (yield 61%).

1. customGas was released from the reaction so care
2. temperaturethe reaction was cooled to room temperature
3. washwashed with water
4. extractionbrine and re-extracted three times with EtOAc
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified with silica gel chromatography (0-5% EtOAc in hexanes)
9. customto yield T18.1 as an oil that
10. customwas used without further purification (yield 61%)

ORD record

ord-a49ad95c5cf94cbcab67e7efa6b6d28c

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748462B2