4-Bromobenzoic acid → 4-Bromo-3-(chlorosulfonyl)benzoic acid

HRID 1927447Notes

Reaction equation

HRID 1927447 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1>>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 114644-Bromobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 37373734-Bromo-3-(chlorosulfonyl)benzoic acid

Conditions

Temperature
110 °C

Procedure

Chlorosulfonic acid (70 mL, 1.05 mol) cooled to 0° C. was added dropwise with stirring to 4-bromo-benzoic acid (50 g, 0.29 mol). The reaction mixture was heated at 110° C. for 10 h, cooled to room temperature and poured onto crushed ice slowly with stirring. The title compound obtained was filtered, washed with water and dried. Yield: 51 g, (84%); mp: 198-199° C.; MS: m/e (EI+) 299 (M+).

Workup

  1. additionwas added dropwise
  2. temperaturecooled to room temperature
  3. additionpoured
  4. customonto crushed ice slowly

Sources & evidence

ORD record
ord-f8c2640eb6f64a4a92788a6943c1097c
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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