Potassium Iodide → HCID 20067142, compound

HRID 358888Notes

Reaction equation

HRID 358888 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:9][CH2:10][CH2:11]Br.[F:13][C:14]1[C:15]([O:28][CH3:29])=[C:16]([CH:24]=[CH:25][C:26]=1[F:27])[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20]>CN(C)C=O>[F:13][C:14]1[C:15]([O:28][CH3:29])=[C:16]([CH:24]=[CH:25][C:26]=1[F:27])[N:17]([CH2:11][CH2:10][F:9])[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 20067155HCID 20067155, compound

Product 1

HCID 20067142HCID 20067142, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2.44 g (0.018 mole) of potassium carbonate, a catalytic amount of potassium iodide and 1.80 g (0.014 mole) of 2-fluoroethyl bromide were added to a solution of 3.00 g (0.012 mole) of 3,4-difluoro-2-methoxy-N-(trifluoroacetyl)aniline (XI) [prepared as described in Step (C1) above] dissolved in 50 ml of dimethylformamide. The mixture was then stirred at 65° C. for 5 hours. At the end of this time, the solvent was distilled off from the mixture under reduced pressure. The residue was extracted with ethyl acetate and purified by column chromatography through silica gel eluted with toluene, to give 0.69 g of 3,4-difluoro-N-(2-fluoroethyl)-2-methoxy-N-(trifluoroacetyl)aniline (XII, R9' =2-fluoroethyl) as a colorless oil.

Workup

  1. distillationAt the end of this time, the solvent was distilled off from the mixture under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. custompurified by column chromatography through silica gel
  4. washeluted with toluene

Sources & evidence

ORD record
ord-2ee0fb421a764e4d9b41c780ca0819b7
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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