1,3-Difluorobenzene → 4-(2,4-Difluorobenzoyl)piperidine-1-carbaldehyde

HRID 2417700Notes

Reaction equation

HRID 2417700 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]([N:7]1[CH2:15][CH2:14][CH:10]([C:11](Cl)=[O:12])[CH2:9][CH2:8]1)=[O:6].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1>>[F:16][C:17]1[CH:18]=[C:19]([F:23])[CH:20]=[CH:21][C:22]=1[C:11]([CH:10]1[CH2:14][CH2:15][N:7]([CH:5]=[O:6])[CH2:8][CH2:9]1)=[O:12]

Participants

4

Reactant 3

HCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 132242561-Formylpiperidine-4-carbonyl chloride

Product 1

HCID 114141024-(2,4-Difluorobenzoyl)piperidine-1-carbaldehydeYield 32.3%

Procedure

To a slurry of 39 g of aluminum chloride and 120 ml of 1,3-difluorobenzene was added dropwise, with stirring, 30 g of N-formylisonipecotic acid chloride. The reaction mixture was stirred under reflux for two hrs and poured into 1 l of ice-water. The mixture was extracted with 4 350-ml portions of chloroform. The combined organic extracts were washed with 2 300-ml portions of water, dried, filtered and evaporated. Trituration with petroleum ether and washing with ether at 0°, yielded 14 g (32.3%) of product, mp, 75°.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for two hrs
  3. extractionThe mixture was extracted with 4 350-ml portions of chloroform
  4. washThe combined organic extracts were washed with 2 300-ml portions of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. washTrituration with petroleum ether and washing with ether at 0°

Sources & evidence

ORD record
ord-1cd4f10c58fc4ee69129d979e5e57d2a
Source dataset
uspto-grants-1984_09
Patent number
US04469869

Reaction notes

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