Sulfuryl chloride → 4-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 1081345Notes

Reaction equation

HRID 1081345 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[C:6]1([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[CH2:13]([O:12][C:6]1[CH:11]=[CH:10][C:9]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:8][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 70352Benzyl Phenyl Ether

Product 1

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 0.87 g of dimethylformamide, at 0° C. under an atmosphere of nitrogen, was added 1.61 g of sulfuryl chloride. The mixture was stirred for 15 min and treated with 2.00 g of benzyl phenyl ether. The mixture was then heated at 100° C. for 1.5 h, cooled to about 40° C., poured onto ice, extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by low pressure silica gel chromatography using 10% ethyl acetate in hexane as eluent to provide 0.78 g of the title product as a white solid. TLC: Rf=0.46, 10% ethyl acetate in hexane. (1H)-NMR (CDCl3) consistent with structure.

Workup

  1. temperaturecooled to about 40° C.
  2. additionpoured onto ice
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by low pressure silica gel chromatography

Sources & evidence

ORD record
ord-0bbbe2fb5d8e49dcb7e400ea2c09d49c
Source dataset
uspto-grants-1996_12
Patent number
US05585397

Reaction notes

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