Phosphorus oxide (P4O10) → 2-Bromo-4-methylbenzonitrile

HRID 657318

Reaction equation

HRID 657318 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 2623402-Bromo-4-methylbenzamide

Product 1

HCID 8208022-Bromo-4-methylbenzonitrileYield 98.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-bromo-4-methylbenzamide (14.8 g, 69.1 mmol) in CHCl3 was added phosphorous pentoxide (24.5 g, 172.8 mmol) and the mixture keep refluxing for 12 h. The reaction was allowed to cool to room temperature, and put into the ice water under the condition of stirring. The organic layer was separated and the aqueous layer was extracted with CHCl3 (150 mL×2). The combined organic phase was washed with brine, and dried over Na2SO4. Evaporation of the solvent afforded the title compound, 2-bromo-4-methylbenzonitrile (13.3 g, 98%). 1H NMR (400 MHz, CDCl3) δ 2.41 (s, 3H), 7.20 (d, J=8.0 Hz, 1H), 7.51-7.54 (m, 2H).

Workup

  1. temperaturethe mixture keep refluxing for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CHCl3 (150 mL×2)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f637d1edd4b24da9b5818382c10f00b0
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Linked notes

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