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

HRID 363048

Reaction equation

HRID 363048 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
100 °C

Procedure

To a 0° C. solution of sulfonyl chloride (1.9 mL, 23.8 mmol) in 2 mL of DMF was added 4.0 g (21.7 mmol) of benzyl phenyl ether (24-1). The resulting solution was then heated at 100° C. for 2 h. The reaction mixture was then cooled and poured onto crushed ice. The aqueous layer was extracted with CH2Cl2 (x3). The combined organic extracts were dried (Na2SO4) and concentrated. Column chromatography (95:5 Hexane/EtOAc) and trituration (hexane) of the pure fractions afforded 24-2 as a pink solid.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionpoured
  3. customonto crushed ice
  4. extractionThe aqueous layer was extracted with CH2Cl2 (x3)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c64f0a7157d94fdfb0a6656623c089b3
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Linked notes

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