Thionyl Chloride → 4'-Methoxybiphenyl-4-sulfonyl chloride

HRID 1964799Notes

Reaction equation

HRID 1964799 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([OH:18])(=O)=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([Cl:21])(=[O:18])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 234334014'-Methoxy[1,1'-biphenyl]-4-sulfonic acid

Product 1

HCID 27947504'-Methoxybiphenyl-4-sulfonyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4′-methoxy[1,1′-biphenyl]-4-sulfonic acid (30 g, 0.11 mol) and thionylchloride (90 ml), DMF (1 ml) was added and the reaction mixture was refluxed for 6 h. Excess thionylchloride was distilled off and the crude was purified by column chromatography over silica gel (pet. ether/CHCl3, 1:1) to give 4′-methoxy[1,1′-biphenyl]-4-sulfonyl chloride (30 g, 95%).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was refluxed for 6 h
  3. distillationExcess thionylchloride was distilled off
  4. customthe crude was purified by column chromatography over silica gel (pet. ether/CHCl3, 1:1)

Sources & evidence

ORD record
ord-f8a0d384ca5d4d08bda8575ab7f16fe2
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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