Phosphorus oxide (P4O10) → 3-Bromo-5-methylbenzonitrile

HRID 564465Notes

Reaction equation

HRID 564465 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([NH2:7])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]#[N:7]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 578133983-Bromo-5-methylbenzamide

Product 1

HCID 145678583-Bromo-5-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 3-bromo-5-methylbenzamide (15.0 g, 70.1 mmol) in CHCl3 was added phosphorous pentoxide (29.8 g, 210.2 mmol) and the mixture was kept refluxing for 2 days (monitored by TLC). 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 dichloromethane (150 mL×2). The combined extracts were washed with brine, dried over NaSO4. The product, 3-bromo-5-methylbenzonitrile (7.20 g, 52%), was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): δ 7.60-7.56 (m, 2 H), 7.40-7.39 (m, 1 H), 2.39 (s, 3 H).

Workup

  1. temperaturethe mixture was kept refluxing for 2 days (monitored by TLC)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (150 mL×2)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over NaSO4
  6. customThe product, 3-bromo-5-methylbenzonitrile (7.20 g, 52%), was purified by flash column chromatography

Sources & evidence

ORD record
ord-8a7d8e2d8ff048cb9fc5a0c9a9aa28d6
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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