Potassium Carbonate → Methyl (4'-hydroxybiphenyl-3-yl)acetate
Reaktionsgleichung
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([C:22]2[CH:23]=[CH:18][CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=2)=[CH:14][CH:13]=1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
10 g of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol and 12.5 g of methyl 3-bromophenylacetate were dissolved in 150 ml of 1,2-dimethoxyethane, then 14 g of potassium carbonate and 920 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred overnight at 70° C. in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 10.336 g of the title compound in the 2:1 hexane-ethyl acetate fraction.
Aufarbeitung
- washwashed with 1N hydrochloric acid
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-78e8d93d603e49c2bc5b378c16cee729
- Quelldatensatz
- uspto-grants-2010_03
- Patentnummer
- US07687664B2
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