Toluene → 2-Fluoro-5-trifluoromethylbenzylisocyanate

HRID 277780

Reaction equation

HRID 277780 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][NH2:5].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:30](Cl)(Cl)=[O:31].C1(C)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH2:4][N:5]=[C:30]=[O:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 88675Proton spongeHCID 5338392-Fluoro-5-(trifluoromethyl)benzylamine

Product 1

HCID 226259052-Fluoro-5-trifluoromethylbenzylisocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a methylene chloride solution of commercially available 2-fluoro-5-trifluoromethyl benzyl amine(5.23 mmol) at 0° C. was added solid Proton sponge (5.23 mmol) then a 20% solution of phosgene in toluene (5.23 mmol). The solution was stirred at 25° C. for 1 hour and then washed with 1N HCl (40 mL). The methylene chloride was then dried with sodium sulfate and evaporated to provide the title compound. 1H-NMR (CDCl3): 7.7 ppm (t, 1H); 7.60 ppm (m, 1H); 7.2 ppm (m, 1H); 4.64 ppm (s, 2H).

Workup

  1. washwashed with 1N HCl (40 mL)
  2. dry with materialThe methylene chloride was then dried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-d8cf9279991d4c7888dd011fbdfbe3ab
Source dataset
uspto-grants-2002_03
Patent number
US06358956B1

Linked notes

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