Formic Acid → 3,5-Difluorobenzaldehyde

HRID 247414Notes

Reaction equation

HRID 247414 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#N.C(O)=[O:12]>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:12]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 5872043,5-Difluorobenzonitrile

Product 1

HCID 5881603,5-DifluorobenzaldehydeYield 55%

Procedure

A mixture of 3,5-difluorobenzonitrile (0.108 mol) and Raney alloy (15 g) was refluxed 2 hours in 90% formic acid (150 ml). The reaction was filtered hot and the filter cake was washed with water, then hexane. The filtrate was extracted three times with hexane, the combined hexane extracts were washed with water and dried over sodium sulfate. Concentration yielded 8.4 g (55%) of a yellow oil.

Workup

  1. filtrationThe reaction was filtered hot
  2. washthe filter cake was washed with water
  3. extractionThe filtrate was extracted three times with hexane
  4. washthe combined hexane extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-8815fffbf71e45bcb0994e7eb1435fd5
Source dataset
uspto-grants-1987_11
Patent number
US04707488

Reaction notes

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