Hexane → HCID 22933545, compound

A solution of 6-chloro-2-fluoro-3-methylphenol (9.00 g, 56.1 mmol) in dichloromethane (100 ml) was added dropwise to a suspension of 85% nitronium•tetrafluoroborate (9.50 g, 60.8 mmol) in dichloromethane (150 ml) at 0 to 5° C. under ice-cooling. The resulting mixture was warmed up to room temperature and stirred for 2 hours while maintaining the temperature. The mixture was poured into ice water and then partitioned and extracted with chloroform, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. After the crude product was dissolved in toluene (57 ml) by heating to 80° C., the solution was allowed to cool to 60° C. and maintained at this temperature. Hexane (171 ml) was added dropwise thereto and the resulting mixture was allowed to cool to room temperature and then it was ice-cooled while maintaining temperature. Thereafter, the crystals formed were collected by filtration and dried to obtain 6-chloro-2-fluoro-3-methyl-4-nitrophenol (7.05 g, 61%).

1. temperaturecooling
2. temperaturewhile maintaining the temperature
3. custompartitioned
4. extractionextracted with chloroform
5. washthe organic layer was washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customto obtain a crude product
10. temperatureby heating to 80° C.
11. temperatureto cool to 60° C.
12. temperaturemaintained at this temperature
13. temperatureto cool to room temperature
14. temperaturecooled
15. temperaturewhile maintaining temperature
16. customThereafter, the crystals formed
17. filtrationwere collected by filtration
18. customdried

ORD record

ord-d0f14367c36343a0bfc3f42a061ffa40

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2