Water → 3-Fluoro-4-(methylthio)benzaldehyde

HRID 2231117Notes

Reaction equation

HRID 2231117 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+].O>CN(C)C=O>[CH3:11][S:12][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 5880883,4-DifluorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 112752573-Fluoro-4-(methylthio)benzaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-difluorobenzaldehyde (2.8 g, 20 mmol) and sodium thiomethoxide (1.5 g, 20 mmol) in dimethylformamide (20 ml) was heated at 80° C. under an argon atmosphere for 2 hours. The reaction was cooled, poured into water (125 ml) and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate and evaporated. The residue was distilled (bp 110-111° C., 0.5 mm Hg) to give 2.5 g (75%) of the desired aldehyde: Anal. Calc'd. for C8H7FSO (MW 170.21): C, 56.45; H, 4.15; S, 18.84. Found: C, 56.40; H, 4.00; S, 18.90.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated
  5. distillationThe residue was distilled (bp 110-111° C., 0.5 mm Hg)

Sources & evidence

ORD record
ord-c5ef4d6da8cb435e9f3fe9cd174cf4be
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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