2-Methyl-4-(trifluoromethoxy)benzamide → 2-Methyl-4-(trifluoromethoxy)benzonitrile

HRID 842932Notes

Reaction equation

HRID 842932 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

3

Reactant 1

HCID 27755492-Methyl-4-(trifluoromethoxy)benzamide

Product 1

HCID 27755552-Methyl-4-(trifluoromethoxy)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
85 °C

Procedure

2-Methyl-4-trifluoromethoxy-benzamide 14 (2.0 g, 9.1 mmol) was taken up in phosphorus oxychloride (15 mL) and heated to 85° C. for 2 hrs. The excess phosphorus oxychloride was removed under reduced pressure and the resulting residue partitioned between sat. aqueous sodium bicarbonate and ether. The organic layer was dried (sodium sulfate) and concentrated. The residue was passed through silica gel using 25% ether/hexanes to remove trace impurities and yielded a colorless solid (90%). 1H NMR (400 MHz,CDCl3) δ7.65 (d, J=8.4 Hz. 1 H, Ar), 7.17 (s, 1 H, Ar), 7.13 (d, J=8.4 Hz, 1 H, Ar), 2.6 (s, 3 H, CH3).

Workup

  1. customThe excess phosphorus oxychloride was removed under reduced pressure
  2. customthe resulting residue partitioned between sat. aqueous sodium bicarbonate and ether
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customto remove trace impurities

Sources & evidence

ORD record
ord-f7b8a77f0f7344acaf7292443643d8ff
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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