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

HRID 1608920Notes

Reaction equation

HRID 1608920 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-methoxybenzeneYield 100.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 8.8 grams (0.062 mole) of 2-fluoro-4-methoxyaniline in 70 mL of toluene was stirred, and a solution of 12.3 grams (0.062 mole) of trichloromethyl chloroformate in 30 mL of toluene was added dropwise. Upon completion of addition, the reaction mixture was warmed to reflux, where it was stirred for about 18 hours. After this time the reaction mixture was cooled and concentrated under reduced pressure, yielding about 10.4 grams of 2-fluoro-4-methoxyphenyl isocyanate. The product was used immediately in the next reaction.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux
  4. temperatureAfter this time the reaction mixture was cooled
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b670ab7a6864b1491fbd2de08e78e2f
Source dataset
uspto-grants-1995_03
Patent number
US05399543

Reaction notes

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