o-Chlorothiophenol → HCID 21162509, compound

HRID 894243Notes

Reaction equation

HRID 894243 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 80599o-ChlorothiophenolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162509HCID 21162509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

o-Chlorothiophenol (4.5 g., 31 mmoles) and cuprous oxide (2.2 g., 15.5 mmoles) in 100 ml. of dimethylformamide were heated in an oil bath at 170°-175° C. for 1.5 hours, during which time a precipitate formed. 5-Bromofuran-3-carboxylic acid (3 g., 15.7 mmoles) was added and heating continued for 2.5 hours. The reaction mixture was cooled to room temperature, filtered, diluted with 500 ml. of water, acidified with conc. hydrochloric acid and product extracted into 250 ml. of ethyl acetate. The ethyl acetate was back-washed with 150 ml. of water and insolubles removed by filtration. Product was extracted from the ethyl acetate into 150 ml. of 1 N sodium hydroxide, the aqueous phase acidified with conc. hydrochloric acid and product reextracted into 150 ml. of fresh ethyl acetate. The ethyl acetate was back-washed with water and concentrated to an oil (3.5 g.). Recrystallization from ether/hexane gave partially purified product in two crops (575 mg., 403 mg.). These were combined and chromatographed on approximately 150 ml. of silica gel with hexane/5% acetic acid as eluant. Middle fractions afforded purified 5-(2-chlorophenylthio)furan-3-carboxylic acid (490 mg., m.p. 146°-148° C., m/e 254).

Workup

  1. customformed
  2. temperatureheating
  3. filtrationfiltered
  4. additiondiluted with 500 ml
  5. extractionextracted into 250 ml
  6. washThe ethyl acetate was back-washed with 150 ml
  7. customof water and insolubles removed by filtration
  8. extractionProduct was extracted from the ethyl acetate into 150 ml
  9. washThe ethyl acetate was back-washed with water
  10. concentrationconcentrated to an oil (3.5 g.)
  11. customRecrystallization from ether/hexane
  12. customgave partially purified product in two crops (575 mg., 403 mg.)
  13. customchromatographed on approximately 150 ml
  14. customMiddle fractions afforded
  15. custompurified 5-(2-chlorophenylthio)furan-3-carboxylic acid (490 mg., m.p. 146°-148° C., m/e 254)

Sources & evidence

ORD record
ord-0a5df73383ac489694c31a70a7b480ef
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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