Thiophenol → 5-Fluoro-2-(phenylthio)benzoic acid

HRID 435698Notes

Reaction equation

HRID 435698 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:10][C:11]1[CH:12]=[CH:13][C:14](I)=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17]>O.[Cu]>[F: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 131585835-Fluoro-2-iodobenzoic acid

Product 1

HCID 122323445-Fluoro-2-(phenylthio)benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A solution of 150 g of potassium hydroxide in 850 ml of water is treated with 47.5 ml of thiophenol at 55° C under a nitrogen atmosphere. The mixture is stirred for 15 minutes and subsequently treated with 1.9 g of copper powder and 207 g of 5-fluoro-2-iodo-benzoic acid. The mixture is heated under reflux for 7 hours, filtered while hot, cooled and acidified with concentrated hydrochloric acid. The precipitated product is filtered off, washed with water and dried. There is obtained 3-fluoro-6-(phenylthio)-benzoic acid which melts at 146°-148° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 7 hours
  3. filtrationfiltered while hot,
  4. temperaturecooled
  5. filtrationThe precipitated product is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-af96e67ea7bb4697abcd0be9e4193382
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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