Water → 1-((3-Bromo-4-(2,4-difluorophenoxy)phenyl)sulfonyl)pyrrolidine

HRID 930929Notes

Reaction equation

HRID 930929 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[OH:25].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:25][C:19]1[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=1[F:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 867210711-((3-Bromo-4-fluorophenyl)sulfonyl)pyrrolidine

Product 1

HCID 896556201-((3-Bromo-4-(2,4-difluorophenoxy)phenyl)sulfonyl)pyrrolidineYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 299a (250 mg, 0.811 mmol), 2,4-difluorophenol (106 mg, 0.811 mmol) and cesium carbonate (317 mg, 0.973 mmol) in 5 mL dimethylsulfoxide was heated at 110° C. for 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water (2×), saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to give the title compound (278 mg, 82% yield), which was used without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water (2×), saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dd5d30d5d5da4dd58a1ea34a13dcd1f1
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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