Methane → 2-(3-Chlorophenylthio)benzoic acid

HRID 1769174Notes

Reaction equation

HRID 1769174 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].Br[C:8]1[CH:9]=[C:10]([Cl:14])[CH:11]=[CH:12][CH:13]=1.O.[CH4:16].C[S:18]([CH3:20])=O>>[Cl:14][C:10]1[CH:9]=[C:8]([S:18][C:20]2[CH:12]=[CH:13][CH:8]=[CH:9][C:16]=2[C:1]([OH:2])=[O:4])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 5

HCID 297MethaneHCID 679Dimethyl SulfoxideHCID 962WaterHCID 79281-Bromo-3-chlorobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 834292-(3-Chlorophenylthio)benzoic acidYield 86%

Procedure

A mixture of thiosolicyclic acid (50.14 g, 0.33 mol) and cupric acetate (5.0 g) in DMSO (500 mL) was brought to reflux and potassium carbonate (54.3 g) was added in portions. 3-Bromochlorobenzene (42 mL, 0.36 mol) was then added via syringe and the mixture was refluxed for 3 hours. The reaction mixture was poured into water, treated with charcoal and filtered through celite. The filtrate was acidified with concentrated HCl and the precipitate which formed was collected by filtration, washed with water and dried in vacuo at 60° C. to afford 75.01 g (86%) of 2-[(3-chlorophenyl)thio]benzoic acid.

Workup

  1. temperatureto reflux
  2. temperaturethe mixture was refluxed for 3 hours
  3. filtrationfiltered through celite
  4. customthe precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-832b6285415a4842ab042b8814ba3b40
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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