Methanesulfonyl chloride → HCID 21097534, compound

Temperature

50 °C

To a solution of 4-bromo-2,6-difluoroaniline (3.0 g, 14.4 mmol) in pyridine (20 ml) was added methanesulfonyl chloride (2.23 ml, 28.8 mmol) at room temperature. Then the mixture was stirred at 50° C. for 6 hours. After cooing to room temperature, the mixture was concentrated in vacuo. The resulting residue was dissolved in THF (40 ml). To this solution was added 2M aqueous sodium hydroxide solution (40 ml) and the reaction was stirred at room temperature for 4 hours. The mixture was acidified with 2M aqueous HCl solution and the whole was extracted with EtOAc. The organic layer was washed with 2M aqueous HCl solution, brine, and dried over sodium sulfate. After concentration in vacuo, the title compound (4.05 g, 98% yield) was obtained as orange solids.

1. customAfter cooing to room temperature
2. concentrationthe mixture was concentrated in vacuo
3. dissolutionThe resulting residue was dissolved in THF (40 ml)
4. additionTo this solution was added 2M aqueous sodium hydroxide solution (40 ml)
5. stirringthe reaction was stirred at room temperature for 4 hours
6. extractionthe whole was extracted with EtOAc
7. washThe organic layer was washed with 2M aqueous HCl solution, brine
8. dry with materialdried over sodium sulfate
9. concentrationAfter concentration in vacuo

ORD record

ord-12cebce0356e445390e2d505c052f6b8

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622589B2