Thiophenol → 3-Phenylsulfanylthiophene-2-carbaldehyde

HRID 2081755Notes

Reaction equation

HRID 2081755 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:9]1([S:15][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[CH:7]=[O:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 197805133-Phenylsulfanylthiophene-2-carbaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-bromothiophene-2-carboxaldehyde (1.9 g, 10 mMol) in ethanol (15 mL) is added thiophenol (2.2 g, 20 mMol) and powdered potassium carbonate (3.04 g, 22 mMol). The mixture is stirred overnight and concentrated. The residue is partitioned between water and ether. The aqueous layer is washed with ether and the organics combined, dried(MgSO4) and concentrated. Purification by flash column (SiO2, eluted with 3% ethylacetate/hexanes) afforded the desired aldehyde (2.02 g, 92%) as a yellow liquid.

Workup

  1. concentrationconcentrated
  2. customThe residue is partitioned between water and ether
  3. washThe aqueous layer is washed with ether
  4. concentrationdried(MgSO4) and concentrated
  5. customPurification
  6. washby flash column (SiO2, eluted with 3% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-2988e50845fb48159f1867d4c6b5a582
Source dataset
uspto-grants-1993_02
Patent number
US05185363

Reaction notes

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