Sulfuryl chloride → 3-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 2306181Notes

Reaction equation

HRID 2306181 reaction equation
[Br-].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([S:16]([O-:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Mg+2].S(Cl)([Cl:23])(=O)=O>C(Cl)Cl>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([S:16]([Cl:23])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 22966386HCID 22966386, compound

Product 1

HCID 157296493-(Benzyloxy)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Magnesium 3-benzyloxyphenylsulfinate bromide, as described above in Step B, (4.5 g, 14 mmol) was dissolved in dry CH2Cl2 (175 mL) and cooled to 0° C. under argon. Sulfuryl chloride (19 mL of a 1.0 M solution in CH2Cl2, 19 mmol) was added dropwise, and the mixture was stirred for 18 hours at ambient temperature, during which time a precipitate formed. The precipitate was removed by filtration and the filtrate was concentrated under reduced pressure to give the product as a yellow oil.

Workup

  1. customformed
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-973767a9431f4601b10c27bf4cc83112
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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