Chloroform → Ethyl 2,6-difluorobenzene-1-carboximidate

HRID 2050197Notes

Reaction equation

HRID 2050197 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].[B-](F)(F)(F)F.[CH3:17][CH2:18][O+](CC)CC.C(Cl)(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[NH:6])[O:5][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 874392,6-DifluorobenzamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 13730259Ethyl 2,6-difluorobenzene-1-carboximidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,6-Difluorobenzamide (1.56 g) in methylene chloride was added to triethyloxonium fluoborate (1.9 g) in methylene chloride and the mixture stirred for 24 hours. The solution was then washed three times with cold sodium carbonate solution and dried over sodium sulphate. The methylene chloride solution was evaporated to yield an oil. This was mixed with chloroform and the solution filtered from insoluble material. Evaporation of the chloroform gave the ethyl 2,6-difluorobenzimidate as a mobile oil.

Workup

  1. washThe solution was then washed three times with cold sodium carbonate solution
  2. dry with materialdried over sodium sulphate
  3. customThe methylene chloride solution was evaporated
  4. customto yield an oil
  5. filtrationthe solution filtered from insoluble material
  6. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-72431eb1f88f400994e63823c8b9c124
Source dataset
uspto-grants-1980_04
Patent number
US04200653

Reaction notes

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