2-Bromobenzoic acid → 2-Bromo-5-(chlorosulfonyl)benzoic acid

HRID 1846044Notes

Reaction equation

HRID 1846044 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 69402-Bromobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 34272982-Bromo-5-(chlorosulfonyl)benzoic acidYield 95%

Procedure

To chlorosulfonic acid (100 mL) cooled to 0° C. was added 2-bromobenzoic acid (20.0 g, 99.5 mmol) portionwise over 10 minutes. The reaction mixture was warmed to room temperature and then to reflux cautiously over 30 minutes in 10° C. increments, followed by reflux for 16 hours. After cooling to room temperature the solution was quenched in 1 mL portions into ice-water (2 L). Further ice was added as necessary to keep the temperature below 5° C. The resulting precipitate was filtered under vacuum and dried in a vacuum oven for 4 hours to give the title compound as a tan solid in 95% yield, 28.6 g.

Workup

  1. temperatureto reflux cautiously over 30 minutes in 10° C. increments
  2. temperatureby reflux for 16 hours
  3. temperatureAfter cooling to room temperature the solution
  4. customwas quenched in 1 mL portions into ice-water (2 L)
  5. additionFurther ice was added as necessary
  6. customthe temperature below 5° C
  7. filtrationThe resulting precipitate was filtered under vacuum
  8. customdried in a vacuum oven for 4 hours

Sources & evidence

ORD record
ord-8c466ebe0e994096972ed3fe0a613e65
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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