Ethyl Acetate → 3-Fluoro-4-(methylthio)benzaldehyde

HRID 1359531Notes

Reaction equation

HRID 1359531 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[CH3:11][S-:12].[Na+].C(OCC)(=O)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:12][CH3:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5880883,4-DifluorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 112752573-Fluoro-4-(methylthio)benzaldehydeYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 3,4-diflourobenzaldehyde (52.1 g, 0.36 mol) was dissolved in acetonitrile (500 mL). Sodium thiomethoxide (25.6 g, 0.36 mol) was added in four equal portions at 15 minute intervals. The slightly exothermic reaction was stirred at room temperature for 4 hours. The reaction mixture was poured into ethyl acetate (500 mL) and extracted with saturated sodium bicarbonate (2×200 mL) followed by saturated ammounium chloride (2×100 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The 3-flouro-4-(methylthio)-benzaldehyde (38.5 g, 0.22 mol) was isolated by vacuum distillation (135-145° C. at 25 mm Hg) as clear liquid. (61% yield) ESHRMS m/z 171.0302 (calcd for M+H, 171.0280).

Workup

  1. customThe slightly exothermic reaction
  2. extractionextracted with saturated sodium bicarbonate (2×200 mL)
  3. dry with materialThe solution was dried over sodium sulfate and solvent
  4. customremoved at reduced pressure

Sources & evidence

ORD record
ord-f26358b1b0944ce7919d71afb6f9320e
Source dataset
uspto-grants-2003_07
Patent number
US06600052B1

Reaction notes

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