Phosphorus oxychloride → 2-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanenitrile

HRID 1156424Notes

Reaction equation

HRID 1156424 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([NH2:16])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:1][C:2]([F:22])([F:23])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]#[N:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12905997HCID 12905997, compound

Product 1

HCID 128048432-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution containing 6.2 g (0.02 mole) of 2-[4-(4-trifluoromethylphenoxy)phenoxy] propanamide and 10.0 ml of phosphorus oxychloride in 50 ml of toluene is stirred at 50° until reaction is complete, as indictated by vpc techniques. The reaction mixture is cooled and poured into crushed ice, whereupon the toluene layer is washed with water, dried, and concentrated in vacuo. Purification is effected by elution through a pad of silica gel (50% toluene/hexane) to afford a colorless solid, mp 53°-56°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured
  3. custominto crushed ice
  4. washwhereupon the toluene layer is washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washis effected by elution through a pad of silica gel (50% toluene/hexane)
  9. customto afford a colorless solid, mp 53°-56°

Sources & evidence

ORD record
ord-b427fb2230904fbf873801238fe8884d
Source dataset
uspto-grants-1982_06
Patent number
US04335249

Reaction notes

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