Potassium Carbonate → 2-(Thiophen-2-ylsulfanyl)benzaldehyde

HRID 1944405Notes

Reaction equation

HRID 1944405 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].C(=O)([O-])[O-].[K+].[K+].F[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 5226742-Thiophenethiol

Product 1

HCID 203898632-(Thiophen-2-ylsulfanyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of thiophene-2-thiol (1.5 mL), potassium carbonate (8.0 g) and N,N-dimethylformamide was treated dropwise with 2-fluorobenzaldehyde (1.7 mL), and the resulting mixture was stirred at room temperature for 42 hours. The mixture was treated with ice/water, extracted with ethyl acetate and the combined organic extract was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 9:1 by volume), followed by distillation at 50° C./11 mbar to afford the title compound as a red oil (1.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe combined organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 9:1 by volume)
  7. distillationfollowed by distillation at 50° C./11 mbar

Sources & evidence

ORD record
ord-abfa6b76baa74541918b12f14a7a570e
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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