Diphosgene → 4-Chloro-2-fluorophenyl isocyanate

HRID 1608032Notes

Reaction equation

HRID 1608032 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.Cl[C:11](OC(Cl)(Cl)Cl)=[O:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:11]=[O:12])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 45582034-Chloro-2-fluorophenyl isocyanateYield 97.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 20.0 g (0.13 mole) of 4-chloro-2-fluoroaniline in 250 ml of toluene was added dropwise a solution of 17.2 ml (0.13 mole) of trichloromethyl chloroformate in 40 ml of toluene. Upon completion of addition the reaction mixture was heated to reflux where it stirred for 16 hours. The solvent was separated from the reaction mixture by distillation to yield 21.8 g of 4-chloro-2-fluorophenyl isocyanate as an oil. The reaction was repeated several times.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux where it
  4. customThe solvent was separated from the reaction mixture by distillation

Sources & evidence

ORD record
ord-f2889680017d4328a9a4835684653cb0
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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