Carbonyl fluoride → 4-Chloro-2-(trifluoromethyl)phenyl carbamic fluoride

HRID 1979628

Reaction equation

HRID 1979628 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.F.C(F)([F:18])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([F:18])=[O:10])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

4

Reactant 3

HCID 9623Carbonyl fluorideHCID 14917Hydrofluoric Acid2×HCID 27332644-Chloro-2-(trifluoromethyl)phenyl isocyanate

Product 1

HCID 204396074-Chloro-2-(trifluoromethyl)phenyl carbamic fluoride

Conditions

Temperature
24 °C

Procedure

4-Chloro-2-(trifluoromethyl)phenyl carbamic fluoride was prepared in situ by the reaction of 221 parts of 4-chloro-2-(trifluoromethyl)-isocyanatobenzene and 380 parts of hydrogen fluoride added over a period of about 15 minutes at about 4° C. The reaction mixture was then sealed in a polytetrafluoroethylene reactor, heated to about 24° C. and maintained at about that temperature, with agitation, for about 96 hours. The reactor was then opened to atmospheric pressure and most of the hydrogen fluoride and carbonyl fluoride gases removed. Analysis of the remaining organic product by gas chromatographic techniques, using n-pentadecane as an internal standard, indicated as yield of 55 parts of 4-chloro-2-(trifluoromethyl)benzenamine.

Workup

  1. additionadded over a period of about 15 minutes at about 4° C
  2. customThe reaction mixture was then sealed in a polytetrafluoroethylene reactor
  3. temperaturemaintained at about that temperature, with agitation, for about 96 hours
  4. customremoved

Sources & evidence

ORD record
ord-3992da07c5554303858bc646bce42752
Source dataset
uspto-grants-1984_11
Patent number
US04481370

Linked notes

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