Thiophenol → 3-Bromo-6-(phenylthio)-benzoic acid

HRID 435690Notes

Reaction equation

HRID 435690 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:12]=[CH:13][C:14](I)=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17]>O.[Cu]>[Br:10][C:11]1[CH:19]=[C:15]([C:14]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:12]=1)[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 3029395-Bromo-2-iodobenzoic acid

Product 1

HCID 214560473-Bromo-6-(phenylthio)-benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A solution of 400 g of potassium hydroxide in 3 litres of water is treated at 45° C under a nitrogen atmosphere with 179 ml of thiophenol and the mixture is stirred for 15 minutes. After the addition of 7.1 g of copper powder and 564 g of 5-bromo-2-iodo-benzoic acid, the resulting mixture is heated under reflux for 5 hours and subsequently filtered while hot, acidified while cooling with 420 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The organic solution is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. There is obtained 3-bromo-6-(phenylthio)-benzoic acid of melting point 171°-173° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 5 hours
  3. filtrationsubsequently filtered while hot,
  4. temperaturewhile cooling with 420 ml of concentrated hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic solution is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-362a111bdedc456b86dc2777fc6d9893
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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