2-Chlorobenzoic Acid → Benzoic acid, 2-chloro-5-(chlorosulfonyl)-

HRID 508790Notes

Reaction equation

HRID 508790 reaction equation
[Cl: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]>>[Cl: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 83742-Chlorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chlorobenzoic acid (5.0 g, 31.93 mmol) was slowly added chlorosulphonic acid (25 mL). The reaction mixture was heated at 100° C. for 5-6 h, followed by stirring at RT for 24 h. The reaction mass was quenched in ice cold water slowly and the solid obtained was filtered off, washed with water and dried to afford 4.0 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 7.50 (d, J=7.8 Hz, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.96 (d, J=1.5 Hz, 1H), 12.69-12.94 (br s, 1H).

Workup

  1. customThe reaction mass was quenched in ice cold water slowly
  2. customthe solid obtained
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f3df8ac3c92949a98bd7746a7d908b4f
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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