Phosphorus oxychloride → 3-(Propan-2-yl)benzonitrile

HRID 2274939Notes

Reaction equation

HRID 2274939 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=O)([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl>>[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]#[N:9])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2579543-(Propan-2-yl)benzamide

Product 1

HCID 2584403-(Propan-2-yl)benzonitrileYield 80.4%

Procedure

A solution of the above amide (4.20 g, 25.7 mmol) in POCl3 (36.0 g, 236 mmol) was stirred at 80° C. for 18 h. The solution was concentrated and the residue was poured into water (100 mL). The mixture was exacted with EtOAc. The organic layers were combined, washed by brine, dried over Na2SO4 and concentrated to give 3-isopropyl-benzonitrile (3.00 g, 80%).

Workup

  1. concentrationThe solution was concentrated
  2. additionthe residue was poured into water (100 mL)
  3. washwashed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d7d3c1cee680421789a3efc937f0a776
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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