Hexane → Ethyl 2-fluoro-3-vinylbenzoate

HRID 658106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658106
Br[C:2]1[C:3]([F:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:15].CCCCCC.[F-].[K+]>C([Sn](CCCC)(CCCC)C=C)CCC.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:13][C:3]1[C:2]([CH:14]=[CH2:15])=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

9

Edukt 4

HCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 17832538Ethyl 3-bromo-2-fluorobenzoate

Produkt 1

HCID 68451554Ethyl 2-fluoro-3-vinylbenzoateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 81998TributylvinyltinLösungsmittel

Versuchsvorschrift

A 12.76 g portion of ethyl 3-bromo-2-fluorobenzoate was dissolved in 50 ml of Tol solution, 15.8 ml of tributyl(vinyl)tin, 236 mg of tris(dibenzylideneacetone)dipalladium and 1.25 ml of tri-tert-butylphosphine 10 wt % hexane solution were added thereto in order, and stirred at room temperature for 13 hours in an atmosphere of argon. This was diluted with 300 ml of diethyl ether, mixed with 25 g of potassium fluoride and 5 ml of purified water and stirred for 30 minutes, the insoluble matter was filtered using a Kiriyama funnel, and then the mother liquid was concentrated. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate=40:1) to obtain 10.3 g (97%) of ethyl 2-fluoro-3-vinylbenzoate (Reference Example 17-1).

Aufarbeitung

  1. additionwere added
  2. stirringstirred for 30 minutes
  3. filtrationthe insoluble matter was filtered
  4. concentrationthe mother liquid was concentrated
  5. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-55c5804f981f4e779883f8eefa040d26
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076367B2

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