Phenol → HCID 13514828, compound

HRID 930880Notes

Reaction equation

HRID 930880 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>CN(C)C=O>[N+:21]([C:12]1[CH:13]=[C:14]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:15]=[CH:16][C:11]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 13514828HCID 13514828, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenol (1.282 g, 13.63 mmol) in dimethylformamide (20 mL) was treated with 60% sodium hydride (0.545 g, 13.63 mmol). The reaction mixture was stirred for 10 minutes. To this solution was added 4-fluoro-3-nitrobenzenesulfonamide (0.75 g, 3.41 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was neutralized with 10% HCl and extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (1:1 ethyl acetate/hexanes) on silica gel to give 0.96 g of the title product.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. extractionextracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (1:1 ethyl acetate/hexanes) on silica gel

Sources & evidence

ORD record
ord-a42e1e1bb64a4bdf90fc08eda1b4c481
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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