Potassium Carbonate → 2-(Methylthio)benzaldehyde

HRID 1893127Notes

Reaction equation

HRID 1893127 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[S-2:16].[CH3:17][Na]>CN(C=O)C>[CH3:17][S:16][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 67970o-FluorobenzaldehydeHCID 178477781HCID 178477781, compound

Product 1

HCID 2864432-(Methylthio)benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

2-fluoro-benzaldehyde (2.00 g, 16.1 mmol), potassium carbonate (2.45 g, 17.7 mmol) and methyl sodium sulfide (17.1 mmol) were dissolved in 10.0 mL DMF in a 50 mL round-bottomed flask under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 55° C. for 24 hr. After cooling, the mixture was added to 50 mL of saturated potassium carbonate solution and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 1:1 dichloromethane/n-hexane as eluent to give a yellow oil (2.08 g, 85%). 1H NMR (200 MHz, CDCl3): δ 2.49 (s, 3H), 7.24-7.58 (m, 3H), 7.80 (dd, J1=7.6, J2=1.4, 1H), 10.25 (s, 1H) ppm.

Workup

  1. customtopped with a reflux condenser
  2. temperatureAfter cooling
  3. extractionextracted with 3×50 mL portions of ether
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. customevaporated
  6. customThe crude product was further purified by chromatography on silica gel using 1:1 dichloromethane/n-hexane as eluent

Sources & evidence

ORD record
ord-f25d0f308a6545f383bacc3a622496ab
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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