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

HRID 1834358Notes

Reaction equation

HRID 1834358 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 indicated 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-1e23ff5c7fb04612b7fd3c72ae18f358
Source dataset
uspto-grants-1978_01
Patent number
US04070178

Reaction notes

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