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

HRID 1073

Reaction equation

HRID 1073 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=O)C>[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 chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A 1.12 portion of anhydrous DMF is cooled to 0° C. and treated dropwise with 2.06 g of sulfuryl chloride. The resulting suspension is stirred for 30 min., then treated with 1.50 g of benzyl phenyl ether. The mixture is heated at 90° C. for 3 h, then cooled, extracted with brine and methylene chloride, and dried over MgSO4. Chormotography on silica gel (i-PrOH/hexanes) yields 4-benzyloxybenzenesulfonyl chloride.

Workup

  1. temperaturecooled
  2. extractionextracted with brine and methylene chloride
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7b357d5bf4334f0fb405475a558ece52
Source dataset
uspto-grants-1998_03
Patent number
US05723490

Linked notes

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