Iodine → HCID 67836504, compound

HRID 1196766Notes

Reaction equation

HRID 1196766 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].II.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[C:13]#[N:14].[Cl-].[NH4+]>O1CCCC1.[Zn]>[NH2:14][C:13]([C:12]1[C:11]([F:10])=[CH:18][CH:17]=[CH:16][C:15]=1[F:19])=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 807IodineHCID 7748Ethyl bromoacetate2×HCID 25517Ammonium ChlorideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 67836504HCID 67836504, compoundYield 404.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 g of ethyl α-bromoacetate and a trace amount of iodine were added to a solution of 18.3 g of zinc in 250 ml of tetrahydrofuran under reflux and vigorously stirred to start the reaction. The reaction solution was cooled to room temperature and added with a 30 ml tetrahydrofuran solution of 13.9 g of 2,6-difluorobenzonitrile at one time. Then 17.8 g of ethyl α-bromoacetate was added dropwise at such a rate that slow refluxing would continue. The reaction solution was further refluxed for one hour, cooled, added into 350 ml of an aqueous solution of 50.0 g of ammonium chloride and extracted with 300 ml of diethyl ether. The obtained organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 16.5 g of ethyl 3-amino-3-(2,6-difluorophenyl)-2-propenoate.

Workup

  1. temperatureunder reflux
  2. customthe reaction
  3. temperaturethat slow refluxing would
  4. temperatureThe reaction solution was further refluxed for one hour
  5. temperaturecooled
  6. extractionextracted with 300 ml of diethyl ether
  7. washThe obtained organic layer was washed with a sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThen the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-a39016e6785e49cc86cc817f465884f5
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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