Cesium carbonate → 1,3-Dibromo-5-monofluoromethoxybenzene

To a tared, sealed 350 mL round-bottomed pressure flask containing a suspension of 3,5-dibromophenol (10.0 g, 39.7 mmol; see step (ii) above) and Cs2CO3 (20.7 g, 63.5 mmol) in DMF (150 mL) at −78° C. was added chlorofluoromethane via bubbling for 5 min through the septum. The septum was replaced with a Teflon stopper and the flask was then sealed and allowed to warm to room temperature where the flask was weighed and determined to contain 9.0 g (131 mmol) of chlorofluoromethane. The solution was heated in an oil bath set at 70° C. overnight. The flask was cooled to room temperature, the pressure cautiously released and the contents diluted with water (100 mL). The aqueous layer was extracted with Et2O (3×200 mL) then, the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with hexanes afforded the sub-title compound. (7.9 g, 71%) as a white solid.

1. customsealed 350 mL round-bottomed pressure flask
2. additioncontaining
3. customvia bubbling for 5 min through the septum
4. customthe flask was then sealed
5. temperatureThe solution was heated in an oil bath
6. temperatureThe flask was cooled to room temperature
7. extractionThe aqueous layer was extracted with Et2O (3×200 mL)
8. dry with materialthe combined organics were dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-b8c559926c78449eb05d6aab792c8e98

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129233B2