Potassium Carbonate → Methyl 2-(4'-methoxybiphenyl-4-yl)-2-phenylacetate

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.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>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a degassed solution of bromide 54 (0.33 g, 1.081 mmol), 4-methoxyphenylboronic acid (0.181 g, 1.190 mmol), POT (0.023 g, 0.076 mmol) and potassium carbonate (0.747 g, 5.41 mmol) in DME (15 mL) and water (7.5 mL) was added Pd(PPh3)4 (0.087 g, 0.076 mmol). The reaction mixture was stirred at 80° C. for 16 h and diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated to afford compound 55 (0.11 g, 31% yield) as a white solid after purification by ISCO (2 to 40% EtOAc/hexane).

Aufarbeitung

washwashed with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-e2be10decd65499dbaa295ca5f3ac0cd
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09096565B2

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