Water → Benzaldehyde, p-phenylthio-

HRID 1177869Notes

Reaction equation

HRID 1177869 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.O>CN(C=O)C.CCCCCC>[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

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 71023Benzaldehyde, p-phenylthio-Yield 96.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Benzenethiol (500 mg, 4.54 mmol) was dissolved in 6 mL of DMF. K2CO3 (940 mg, 6.81 mmol) was added and the resulting mixture was stirred at room temperature for 10 mins. 4-Fluoro-benzaldehyde (675 mg, 5.44 mmol) was then added and the resulting mixture was stirred at 50° C. for 2 hours. The mixture was then stirred at 80° C. for 3 hours. Water was added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 5/95 EtOAc:hexane as the eluent) afforded 940 mg (96% yield) of 4-phenylsulfanyl-benzaldehyde. LC-MS purity: 91.3%

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 2 hours
  2. stirringThe mixture was then stirred at 80° C. for 3 hours
  3. extractionthe product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product
  8. customPurification by column chromatography (

Sources & evidence

ORD record
ord-e6da569d8d2849369d89bb59ab3c6cbf
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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