Dimethylformamide → 1-Benzyloxy-2,3-difluoro-6-nitrobenzene

Temperature

60 °C

In THF (200 ml) was dissolved 2,3-difluoro-6-nitrophenol (10.0 g, 57.1 mmol), followed by the addition of potassium carbonate (15.8 g, 114.2 mmol) and benzyl bromide (7.47 ml, 62.8 mmol) at room temperature. The reaction mixture was stirred at 60° C. for 6 hours. DMF (100 ml) was added to the reaction mixture and the mixture was stirred at 60° C. for 24 hours. After cooling to room temperature, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with ether (100 ml), washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from the hexane/ethyl acetate (4/1) eluate fractions, the title compound (4.17 g, 28%) was obtained as a yellow solid.

1. stirringthe mixture was stirred at 60° C. for 24 hours
2. temperatureAfter cooling to room temperature
3. distillationthe reaction mixture was distilled under reduced pressure
4. customto remove the solvent
5. additionThe residue was diluted with ether (100 ml)
6. washwashed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. distillationdistilled under reduced pressure
9. customto remove the solvent
10. customThe residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from the hexane/ethyl acetate (4/1) eluate fractions

ORD record

ord-36f6bd22e37a4adfa20c5cb84acb128b

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2