Hydrochloric Acid → 3-Fluoro-4-(methylthio)benzaldehyde

HRID 2086631Notes

Reaction equation

HRID 2086631 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+].Cl>CN(C=O)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 313Hydrochloric AcidHCID 5880883,4-DifluorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 112752573-Fluoro-4-(methylthio)benzaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3,4-difluorobenzaldehyde (4.26 g, 30 mmol) and sodium thiomethoxide (2.1 g, 30 mmol) in DMF (40 mL) was heated at 90° C. for 1 hour. After cooling, 2N aqueous HCl was added to the mixture. The whole was extracted with Et2O (70 mL×3), the combined organic layer washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/10) to provide the subtitle compound (3.1 g, 61% yield) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionThe whole was extracted with Et2O (70 mL×3)
  3. washthe combined organic layer washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-0ab7264b3c24445996a6edc76c769d77
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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