Hydrochloric Acid → 4-Bromo-2-sulfanylbenzoic acid

HRID 499439Notes

Reaction equation

HRID 499439 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([S:12]C(N(C)C)=O)[CH:3]=1.[OH-].[Na+].Cl>>[Br:1][C:2]1[CH:3]=[C:4]([SH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59750326Methyl 4-bromo-2-[(dimethylcarbamoyl)sulfanyl]benzoate

Product 1

HCID 166561284-Bromo-2-sulfanylbenzoic acidYield 100%

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-bromo-2-[[(dimethylamino)carbonyl]thio]benzoate (3.2 g, 10 mmol) and 10% aqueous sodium hydroxide solution (20 g, 50 mmol) was stirred at 100° C. for 14 hrs. The reaction mixture was acidified (pH 3) by the addition of 6 N hydrochloric acid. The precipitates were collected by filtration, dissolved in ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (2.3 g, 100%) as white crystals.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-658415cc135847f4929add9ac7d77eb2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…