Potassium Carbonate → 4-Chloro-2-[(4-fluorophenyl)sulfanyl]benzoic acid

HRID 2083765Notes

Reaction equation

HRID 2083765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.I[C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Cl:19][C:17]1[CH:18]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[C:15]([S:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 1394524-Chloro-2-iodobenzoic acid

Product 1

HCID 203575284-Chloro-2-[(4-fluorophenyl)sulfanyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1.28 g. (0.01 mol) of p-fluorothiophenol and 2.82 g. (0.01 mol) of 2-iodo-4-chlorobenzoic acid in 20 ml. of pyridine is added 1.3 g. (0.01 mol) of potassium carbonate, with stirring. Additional pyridine is added until solution is clear and then 0.3 g. of cuprous chloride is introduced. The resulting mixture is refluxed overnight, poured into ice-water, stirred and filtered. The aqueous solution is acidified and filtered. The solid is dissolved in 5% sodium bicarbonate solution and this solution is extracted with ether. The aqueous solution is acidified, extracted with ether and the washed, dried extract is concentrated to give 4-chloro-2-(4-fluorophenylthio)-benzoic acid, m.p. 204°-213° C. The latter (6.5 g., 0.023 mol) is heated for one hour with 105 g. of sulfuric acid to obtain 2-fluoro-6-chloro-9-thioxanthone, m.p 222°-224° C.

Workup

  1. temperatureThe resulting mixture is refluxed overnight
  2. filtrationfiltered
  3. filtrationfiltered
  4. dissolutionThe solid is dissolved in 5% sodium bicarbonate solution
  5. extractionthis solution is extracted with ether
  6. extractionextracted with ether
  7. customthe washed, dried
  8. extractionextract
  9. concentrationis concentrated

Sources & evidence

ORD record
ord-1e16c3fbc57646059c1e94689ed9a037
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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