Reaction #1169

ord-7b357d5bf4334f0fb405475a558ece52

Reaction equation

O=S(=O)(Cl)Cl
sulfuryl chloride
c1ccc(COc2ccccc2)cc1
benzyl phenyl ether
→
O=S(=O)(Cl)c1ccc(OCc2ccccc2)cc1
4-benzyloxybenzenesulfonyl chloride

Reactants

O=S(=O)(Cl)Cl
sulfuryl chloride
c1ccc(COc2ccccc2)cc1
benzyl phenyl ether

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
90°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled
  2. 2
    Extractionextracted with brine and methylene chloride
  3. 3
    Dryingdried over MgSO4

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723490uspto-grants-1998_03