Ethanol → HCID 57667959, compound

HRID 2191697Notes

Reaction equation

HRID 2191697 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8](O)C.Br[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:13]=1.C(=O)([O-])O.[Na+]>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.O.C(OCC)(=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:14]2[CH:13]=[C:12](/[CH:8]=[CH:7]/[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 57667801HCID 57667801, compound

Product 1

HCID 57667959HCID 57667959, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of toluene 2.0 mL, ethanol 0.6 mL and water 0.2 mL of methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added (E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene 0.21 g, sodium hydrogen carbonate 0.18 g and tetrakis(triphenylphosphine)palladium(0) 40 mg, and it was heated and refluxed under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, tetrakis(triphenylphosphine)palladium(0) 40 mg was added to it, and it was heated and refluxed under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid, saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=20:1] to give methyl 2-(4-fluoroanilino)-4-((E)-2-phenylvinyl)benzoate.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed under nitrogen atmosphere for 2 hours
  3. temperaturewas heated
  4. temperaturerefluxed under nitrogen atmosphere for 6 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washafter sequential washing with 1.0 mol/L hydrochloric acid, saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2e161b40b00f4db5afbf3964bf0f4590
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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