Triphosgene → 1-Difluoromethoxy-3-isocyanato-2-methylbenzene

HRID 628492Notes

Reaction equation

HRID 628492 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[C:5]([CH3:11])=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:6]([N:7]=[C:14]=[O:16])[C:5]=1[CH3:11]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 434378993-(Difluoromethoxy)-2-methylaniline

Product 1

HCID 898758031-Difluoromethoxy-3-isocyanato-2-methylbenzeneYield 200.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, to a mixture of 3-difluoromethoxy-2-methylaniline 6.4 g and toluene 100 ml was added triphosgene 5.48 g, and the resulting mixture was stirred with heating under reflux for one hour. The reaction mixture was concentrated under reduced pressure to give 1-difluoromethoxy-3-isocyanato-2-methylbenzene 7.36 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a40e5c5869b2438e8bd5aa4155140b81
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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