Phosphorus pentachloride → 4-(Chloro(isocyanato)methyl)-3-fluorobenzonitrile

HRID 927231Notes

Reaction equation

HRID 927231 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](NC(=O)OCC)[NH:16][C:17](=O)[O:18]CC)=[C:11]([F:28])[CH:10]=1)#[N:8]>C1(C)C=CC=CC=1>[Cl:2][CH:15]([N:16]=[C:17]=[O:18])[C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][C:11]=1[F:28]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 90327812Diethyl(4-Cyano-2-fluorophenyl)methylenedicarbamate2×

Product 1

HCID 903108734-(Chloro(isocyanato)methyl)-3-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorous pentachloride (9.63 g, 46.2 mmol) is added to a mixture of diethyl (4-cyano-2-fluorophenyl)methylenedicarbamate (intermediate 26, 6.50 g, 21.0 mmol) in toluene (25.0 mL), and the mixture is heated at reflux for 3 h. The toluene is evaporated, and the mixture is then purified by distillation under reduced pressure. The first fraction (ca. 35° C., ca. 0.2 mbar) is discarded. The second fraction (ca. 112° C., ca. 0.1 mbar) is collected. Yield: 1.90 g.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 h
  3. customThe toluene is evaporated
  4. distillationthe mixture is then purified by distillation under reduced pressure
  5. customThe first fraction (ca. 35° C., ca. 0.2 mbar)
  6. customThe second fraction (ca. 112° C., ca. 0.1 mbar) is collected

Sources & evidence

ORD record
ord-f288f2b7b0c74a2f98b844ea3974697b
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

Loading…