Thiophenol → Benzaldehyde, p-phenylthio-

HRID 1470632Notes

Reaction equation

HRID 1470632 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>CN(C=O)C>[C:1]1([S:7][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 71023Benzaldehyde, p-phenylthio-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of thiophenol (0.5 g, 0.463 mL, 4.5 mmol) in DMF (6 mL) was added potassium carbonate (0.94 g, 6.8 mmol) and the mixture was stirred at room temperature for 15 minutes. 4-fluoro benzaldehyde (0.675 g, 0.574 mL, 5.4 mmol) was added and the reaction mixture stirred at 80° C. for 6 h. The progress of the reaction was monitored by TLC. The reaction mixture quenched with water (20 mL) and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with water (25 mL×2) then with brine (25 mL), dried over anhydrous sodium sulphate and concentrated. The obtained residue was purified by column chromatography using 5% ethyl acetate in hexane to obtain title compound (0.94 g, 96%).

Workup

  1. stirringthe reaction mixture stirred at 80° C. for 6 h
  2. customThe reaction mixture quenched with water (20 mL)
  3. extractionextracted with ethyl acetate (50 mL×2)
  4. washThe combined organic layers were washed with water (25 mL×2)
  5. dry with materialwith brine (25 mL), dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-f88493568bbe473ca59a11766753aba7
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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