Sodium Carbonate → HCID 117760182, Verbindung

HRID 1049396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049396
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.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]>[CH2:17]([O:16][C:3]1[CH:4]=[C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:2]=1[C:26]1[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:25]=1[F:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

Produkt 1

HCID 117760182HCID 117760182, VerbindungAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmosphere, to a solution of (((4-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene (21.8 g) in toluene (160 mL) were added 2-fluoro-5-methoxyphenylboronic acid (13.8 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.23 g), tris(dibenzylideneacetone)dipalladium(0) (1.24 g) and 2.0 M aqueous sodium carbonate solution (81.0 mL), and the mixture was stirred at 80° C. for 14 hr. The reaction mixture was diluted with water, and filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (22.1 g) as a pale-yellow oil.

Aufarbeitung

  1. filtrationfiltered through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-77cd6b080a0148dea8d021bff30c5beb
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382188B2

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