Toluene → HCID 118308724, compound

HRID 923502Notes

Reaction equation

HRID 923502 reaction equation
Br[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].[C:16]1(C)C=CC=C[CH:17]=1.C(C([Sn])=C(CCCC)CCCC)CCC.[F-].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[F:8][C:7]([F:10])([F:9])[C:6]([NH:5][CH2:4][C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[CH:16]=[CH2:17])=[O:11]

Participants

7

Reactant 4

HCID 1140TolueneHCID 522689Potassium FluorideHCID 53438229Tri(butyl)vinyltinHCID 57470274Acetamide, N-[(2-bromophenyl)methyl]-2,2,2-trifluoro-

Product 1

HCID 118308724HCID 118308724, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Under an argon atmosphere, to a mixture of 2.47 g of N-(2-bromobenzyl)-2,2,2-trifluoroacetamide and 25 ml of toluene were added 1.02 g of tetrakis(triphenylphosphine)palladium(0) and 3.10 g of tributylvinyltin, followed by stirring at 130° C. for 17 hours. The reaction mixture was left to be cooled to room temperature, and ethyl acetate and a 10% aqueous potassium fluoride solution were then added thereto, followed by stirring. The reaction mixture was filtered over Celite and the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.71 g of 2,2,2-trifluoro-N-(2-vinylbenzyl)acetamide.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. stirringby stirring
  4. filtrationThe reaction mixture was filtered over Celite
  5. washthe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04625414846b43089777857b52ef81e6
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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