1,1'-Carbonyldiimidazole → 3-(Difluoromethoxy)benzonitrile

HRID 1380048Notes

Reaction equation

HRID 1380048 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8]O.C1N=CN(C(N2C=NC=C2)=O)C=1>O1CCCC1>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 861304583-(Difluoromethoxy)benzaldehyde Oxime

Product 1

HCID 27369883-(Difluoromethoxy)benzonitrileYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.95 g of 3-(difluoromethoxy)benzaldehyde oxime in 50 ml of dry tetrahydrofuran was treated with 4.30 g of N,N-carbonyldiimidazole. After the effervescence had subsided, the reaction solution was allowed to stand overnight, then concentrated in vacuo. The residue was taken up in 75 ml of water and the pH adjusted to 4 with hydrochloric acid. The nitrile was extracted into ether, dried over sodium sulfate and concentrated, giving a yellow oil which upon distillation gave 2.45 g of the desired compound as a colorless oil, bp 73°-75° C./0.3 mm.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe nitrile was extracted into ether
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customgiving a yellow oil which
  6. distillationupon distillation

Sources & evidence

ORD record
ord-cb07054d23c2499da774432a83e8dbfd
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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