Dimethyl Sulfoxide → HCID 10487663, compound

Oxalyl chloride (0.26 ml) was added at −78° C. to dimethyl sulfoxide (0.42 ml) and dichloromethane (7 ml) and the resultant mixture was stirred at the same temperature for 3 min. Next, the 4,7-difluoro-2-hydroxybenzofuran (272 mg) was added to the mixture at the same temperature followed by stirring for 40 min. After adding triethylamine (1.2 ml) to the liquid reaction mixture, it was heated to room temperature and then stirred at room temperature for additional 30 min. Then water was added to the liquid reaction mixture followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane) to give 4,7-difluorobenzofuran-2-carbaldehyde (169 mg) as a colorless solid.

1. customto the liquid reaction mixture, it
2. stirringstirred at room temperature for additional 30 min
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane)

ORD record

ord-2048eec478c34d26b953e0763eea1fb0

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258811B1