Water → p-(Difluoromethoxy)benzaldehyde

Temperature

140 °C

To a stirred suspension of potassium fluoride (372 mg, 6.4 mmol) in dry DMSO (10 ml) was added a solution of 3-hydroxy-4-difluoromethoxy benzaldehyde (1.0 gm, 5.3 mmol) in DMSO (10 ml). The reaction contents were heated at 140° C. for 10 min. A solution of 2-fluoronitrobenzene (747 mg, 5.3 mmol) in DMSO (5 ml) was added to the above suspension and the reaction mixture was stirred at 140° C. for 3.5 h. The reaction mixture was cooled to room temperature and the contents were poured into water (200 ml) and extracted with ethyl acetate (100 ml×3). The organic extracts were combined and washed with 1N sodium hydroxide (50 ml×2), water and brine and dried over anhydrous sodium sulfite. The dried organic layer was concentrated in vaccuo to obtain 3-2-nitrophenoxy)-4-difluoromethoxy benzaldehyde as a pale yellow solid (1.4 gm).

1. customThe reaction contents
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionextracted with ethyl acetate (100 ml×3)
4. washwashed with 1N sodium hydroxide (50 ml×2), water and brine
5. dry with materialdried over anhydrous sodium sulfite
6. concentrationThe dried organic layer was concentrated in vaccuo

ORD record

ord-5870f7a480e2482aaa4aa489a15b428d

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238725B2