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

HRID 2281279

Reaction equation

HRID 2281279 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-b40b6c01aa504cb085c13f455ac6611a
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Linked notes

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