Diphosgene → 4-(4-Fluorophenylmethoxy)-2-fluorophenyl isocyanate

HRID 257367Notes

Reaction equation

HRID 257367 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[F:17].Cl[C:19](OC(Cl)(Cl)Cl)=[O:20]>C1(C)C=CC=CC=1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([N:1]=[C:19]=[O:20])=[C:3]([F:17])[CH:4]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

Product 1

HCID 189810564-(4-Fluorophenylmethoxy)-2-fluorophenyl isocyanateYield 135.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6.50 g (0.0276 mole) of 4-fluorophenylmethyl 4-amino-3-fluorophenyl ether in toluene, stirring at room temperature, was slowly added 3.95 g (0.020 mole) of trichloromethyl chloroformate. During the addition a thick precipitate formed. Upon completion of addition, the reaction mixture was stirred for one hour at room temperature and then at reflux for approximately seventeen hours. The toluene was removed by distillation, leaving 7.10 g of 4-(4 -fluorophenylmethoxy)-2-fluorophenyl isocyanate.

Workup

  1. additionDuring the addition a thick precipitate
  2. customformed
  3. additionUpon completion of addition
  4. temperatureat reflux for approximately seventeen hours
  5. customThe toluene was removed by distillation

Sources & evidence

ORD record
ord-2eb1c73aaf5140b68f54efd0f1288cf5
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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