Triethylamine → HCID 57804097, compound

HRID 2102895Notes

Reaction equation

HRID 2102895 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.CCN(CC)CC.[F:19][C:20]([F:25])([F:24])[CH:21]=[CH:22][CH3:23].C([O-])([O-])=O.[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C>[F:19][C:20]([F:25])([F:24])[CH2:21][C:22]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)=[CH2:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 27786791,1,1-trifluorobut-2-ene

Product 1

HCID 57804097HCID 57804097, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of methyl 4-iodobenzoate (2.62 g, 10 mmol), Et3N (5 ml), acetonitrile (6 ml), Pd(OAc)2 (100 mg, 0.4 mmol) added 1,1,1-trifluoro-2-butene (2.20 g, 20 mmol) was sealed and heated at 125° C. for 20 h. After cooling, the mixture was treated with sat. Aq. Na2CO3 solution and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography on silica gel to give methyl (e)-methyl 4-(4,4,4-trifluorobut-2-en-2-yl)benzoate and methyl 4-(4,4,4-trifluorobut-1-en-2-yl)benzoate.

Workup

  1. customwas sealed
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b015b98e0952495d9ae5d13c5a0e0ce3
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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