2-Propanethiol → 2-(Isopropylthio)benzaldehyde

HRID 1893125Notes

Reaction equation

HRID 1893125 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+].[CH3:16][CH:17]([SH:19])[CH3:18]>CN(C=O)C>[CH:17]([S:19][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 11430Potassium Carbonate2×HCID 67970o-Fluorobenzaldehyde

Product 1

HCID 112061372-(Isopropylthio)benzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-fluoro-benzaldehyde (2.00 g, 16.1 mmol), potassium carbonate (2.45 g, 17.1 mmol) and 2-propanethiol (1.35 g, 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 50° C. for 48 h. After cooling the mixture was added to 50 mL of saturated potassium carbonate solution, and the mixture was extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The yellow oil residue of the crude product was further purified by chromatography on silica gel using 95:5 petroleum ether (60-80) and dichloromethane as eluent to afford a yellow oil (2.58 g, 89%).

Workup

  1. customtopped with a reflux condenser
  2. temperatureAfter cooling the mixture
  3. extractionthe mixture was extracted with 3×50 mL portions of ether
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. customevaporated
  6. customThe yellow oil residue of the crude product was further purified by chromatography on silica gel using 95:5 petroleum ether (60-80) and dichloromethane as eluent

Sources & evidence

ORD record
ord-d2e33ba4a20c43d39c2bd1c4e572ee96
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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