Dimethylformamide → 4'-Bromobiphenyl-4-sulfonyl chloride

HRID 413363Notes

Reaction equation

HRID 413363 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=O)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:25])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:25])(=[O:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 45247074-BROMO-4'-SULFOBIPHENYL

Product 1

HCID 27568454'-Bromobiphenyl-4-sulfonyl chloride

Procedure

To a solution of 4′-bromobiphenyl-4-sulfonic acid 13a (18.8 g, 78.1 mmol) in thionyl chloride (150 mL) is added a catalytic amount of N,N-dimethylformamide (0.3 mL). The reaction mixture is heated to reflux for 4 hr. The mixture is then cooled to room temperature, and concentrated under reduced pressure. Toluene is then added and the mixture is concentrated under reduced pressure. The solid crude product is then recrystallized with ethyl acetate and hexanes to give the solid desired product.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4 hr
  3. concentrationconcentrated under reduced pressure
  4. additionToluene is then added
  5. concentrationthe mixture is concentrated under reduced pressure
  6. customThe solid crude product is then recrystallized with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-33ab656c678a47d1bde8b4b0f7f06a41
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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