Triethylamine → HCID 57804162, compound

HRID 2102897Notes

Reaction equation

HRID 2102897 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])[C:21]([CH3:23])=[CH2:22].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])/[C:21](/[CH3:23])=[CH:22]/[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 1362141-Propene, 3,3,3-trifluoro-2-methyl-

Product 1

HCID 57804162HCID 57804162, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
125 °C

Procedure

To 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) was added 2-trifluoromethylpropene (2.20 g, 20 mmol). The mixture 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)-4-(3,3,3-trifluoro-2-methylprop-1-enyl)benzoate.

Workup

  1. customThe mixture was 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-22b6bf6ee06046d686a972defae041a4
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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