Diphosgene → p-(Trifluoromethoxy)phenyl isocyanate

HRID 2095492Notes

Reaction equation

HRID 2095492 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.Cl[C:14](OC(Cl)(Cl)Cl)=[O:15]>C1COCC1>[N:8]([C:7]1[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=1)=[C:14]=[O:15]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateYield 164.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.41 ml (3.00 mmol) of 4-(trifluoromethoxy)aniline in 5.4 ml of THF was added 0.22 ml (1.80 mmol) of trichloromethyl chloroformate an heated to reflux for 45 min. The solution was evaporated under reduced pressure, dissolved in toluene and evaporated (2×) to give 0.60 g (99%) of the titled compound as pink solid. MS: 203 M+.

Workup

  1. temperaturean heated
  2. temperatureto reflux for 45 min
  3. customThe solution was evaporated under reduced pressure
  4. dissolutiondissolved in toluene
  5. customevaporated (2×)

Sources & evidence

ORD record
ord-120ce0e26171432c8ca21e2d8cf5df9e
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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