Pentafluoronitrobenzene → 1,2,4,5-Tetrafluoro-3-methoxy-6-nitrobenzene

50 g of pentafluoronitrobenzene was dissolved in 400 ml of dry methanol. Thereto was dropwise added, with ice-cooling, a solution of 13.95 g of sodium methoxide dissolved in 50 ml of dry methanol. A reaction was allowed to take place at room temperature for 2 hours. The reaction mixture was concentrated to a volume of about ⅓ under vacuum. The residue was poured into 500 ml of water. The organic layer was extracted with 300 ml of ether. The ether layer was washed with an aqueous sodium chloride solution and dried over MgSO4. The resulting solution was subjected to vacuum distillation to remove the solvent. The residue was subjected to vacuum distillation (96 to 97° C./0.35 mmHg (47 Pa)) to obtain 38 g of 2,3,5,6-tetrafluoro-4-methoxynitrobenzene (yield: 72%).

1. additionThereto was dropwise added, with ice-
2. temperaturecooling
3. customat room temperature
4. customfor 2 hours
5. concentrationThe reaction mixture was concentrated to a volume of about ⅓ under vacuum
6. additionThe residue was poured into 500 ml of water
7. extractionThe organic layer was extracted with 300 ml of ether
8. washThe ether layer was washed with an aqueous sodium chloride solution
9. dry with materialdried over MgSO4
10. distillationThe resulting solution was subjected to vacuum distillation
11. customto remove the solvent
12. distillationThe residue was subjected to vacuum distillation (96 to 97° C./0.35 mmHg (47 Pa))

ORD record

ord-9b4f7023777043d5a890227bde1e6aa3

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06746722B2