Diphosgene → 2-Fluoro-1-isocyanato-4-methoxybenzene

HRID 2225388Notes

Reaction equation

HRID 2225388 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:12](OC(Cl)(Cl)Cl)=[O:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[N:4]=[C:12]=[O:13]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 37563832-Fluoro-4-methoxyaniline

Product 1

HCID 189810662-Fluoro-1-isocyanato-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 13.75 g (0.0967 mole) of 2-fluoro-4-methoxyaniline in 120 mL of toluene was slowly added over a period of 30 minutes a solution of 19.13 g (0.0967 mole) of trichloromethyl chloroformate in 30 mL of toluene. During the addition the temperature rose to 35° C. The reaction mixture was stirred without external heating for 30 minutes and then heated at reflux for approximately 17 hours. At the end of this time all of the solvent was removed by distillation, leaving 2-fluoro-4-methoxyphenyl isocyanate as a purple liquid, which was used immediately in Step B.

Workup

  1. additionDuring the addition the temperature
  2. customrose to 35° C
  3. temperaturewithout external heating for 30 minutes
  4. temperatureheated
  5. temperatureat reflux for approximately 17 hours
  6. customAt the end of this time all of the solvent was removed by distillation

Sources & evidence

ORD record
ord-1e294066ef8040b89542864cdf285c26
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

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