Chlorosulfonic acid → 849333-58-0

HRID 1173340Notes

Reaction equation

HRID 1173340 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][C:8]=1[CH3:16]>>[Br:6][C:7]1[C:8]([CH3:16])=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:14][C:15]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 45357699849333-58-0

Procedure

Chlorosulfonic acid (150 mL, 2.18 mol) was added slowly to compound of Example 1b (74 g, 0.344 mol) at 0° C. The reaction mixture was refluxed for 4.5 h and then was poured into ice-cold water (1500 mL) with stirring. The solid was filtered, washed with water till filtrate was neutral and dried to obtain the title compound. Yield: 72.40 g (66.8%); 1H NMR (DMSO-d6, 300 MHz): δ 2.40 (s, 3H, CH3), 7.80 (s, 1H, Ar), 8.30 (s, 1H, Ar); MS: m/e (ES−) 315 (M−1).

Workup

  1. temperatureThe reaction mixture was refluxed for 4.5 h
  2. filtrationThe solid was filtered
  3. washwashed with water till filtrate
  4. customdried

Sources & evidence

ORD record
ord-b61c6343a6e743ee91751e1231b27793
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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