Water → 3-Bromo-4-(2,4-difluorophenoxy)benzenesulfonamide

HRID 575603Notes

Reaction equation

HRID 575603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[F:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 790405443-Bromo-4-fluorobenzenesulfonamide

Product 1

HCID 617127003-Bromo-4-(2,4-difluorophenoxy)benzenesulfonamideYield 58.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-bromo-4-fluorobenzenesulfonamide (400 mg, 1.6 mmol) and 2,4-difluorophenol (228 mg, 1.76 mmol) in DMSO (16 ml) was treated with cesium carbonate (1 g, 3.2 mmol). The resulting mixture was heated to 120° C. for 20 min by microwave irriadation (normal). The mixture was treated with water (100 ml) and extracted with EtOAc (3×50 ml). The combined organic extracts were washed with saturated bicarbonate solution (aq), dried over sodium sulfate, filtered and concentrated in vacuo to afford a tan solid. The solid was purified by silica gel chromatography (12 g ISCO, 30% EtOAc in hexanes 30 ml/min) to give the title compound (340 mg, 58%) as a tan solid LCMS (M−H)−=362.

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. washThe combined organic extracts were washed with saturated bicarbonate solution (aq)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a tan solid
  7. customThe solid was purified by silica gel chromatography (12 g ISCO, 30% EtOAc in hexanes 30 ml/min)

Sources & evidence

ORD record
ord-8ecfcdcfcc314c82829a28456d24d686
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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