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

HRID 1846014Notes

Reaction equation

HRID 1846014 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 acid

Conditions

Temperature
115 °C

Procedure

2-Bromobenzoic acid (10.2 g, 50.8 mmol) was added in several portions to chlorosulfonic acid (50 mL) at 0° C. and the resulting solution held at this temperature for 15 minutes. The mixture was then heated at 115° C. for 16 hours. The reaction mixture was cooled to room temperature and was cautiously added drop-wise onto ice. The resulting suspension was allowed to reach room temperature and filtered. The solid was dried under vacuum at 40° C. for 16 hours. The title compound was obtained as a beige solid 85% yield, 12.8 g.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto reach room temperature
  3. filtrationfiltered
  4. customThe solid was dried under vacuum at 40° C. for 16 hours

Sources & evidence

ORD record
ord-aba9ea75e6ef47f086eaa31655f424d3
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…