Potassium Hydroxide → Benzeneacetic acid, 2-[(3-chloro-4-fluorophenyl)thio]-

HRID 1732765Notes

Reaction equation

HRID 1732765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21]>O.[Cu]>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]([OH:22])=[O:21])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 27341973-Chloro-4-fluorobenzene-1-thiolHCID 27800902-Iodophenylacetic acid

Product 1

HCID 12271950Benzeneacetic acid, 2-[(3-chloro-4-fluorophenyl)thio]-Yield 72%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

The thiophenol from the preceding experiment (34.5 g) is added at 50° C. to a solution of potassium hydroxide (40 g) in water (425 ml) and this mixture is stirred until it becomes homogeneous. Then, o-iodophenylacetic acid (55.0 g) and copper powder (2.0 g) are added and the mixture refluxed for 24 hours. While still warm, the solution is filtered with charcoal, the filtrate diluted with water and acidified with hydrochloric acid. The separated crude oily acid is extracted with benzene, the solvent evaporated and the residue crystallized from aqueous ethanol, yielding 45.2 g (72%) of 2-(3-chloro-4-fluorophenylthio)phenylacetic acid which in the pure state melts at 85°-87° C. (cyclohexane-hexane).

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. temperatureWhile still warm
  3. filtrationthe solution is filtered with charcoal
  4. additionthe filtrate diluted with water
  5. customThe separated crude oily acid
  6. extractionis extracted with benzene
  7. customthe solvent evaporated
  8. customthe residue crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-9ba86aae71164abf90f0ded4db876a71
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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