Hydrochloric Acid → 1-(2-Fluorobiphenyl-4-yl)cyclopropanecarboxylic acid

HRID 1879435Notizen

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:14].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:3]1[CH:4]=[C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

800 mg (3.1 mmoles) of 4-bromo-3-fluorophenylcyclopropanecarboxylic acid and 650 mg (3.4 mmoles) of phenylboronic acid are suspended in 8 ml of a 2M K2CO3 aqueous solution. The mixture is added with tetrabutylammonium bromide (960 mg, 3 mmoles) and palladium(II) acetate (40 mg, 0.18 mmoles) and heated at 130° C. in a closed reactor for 30 minutes. After cooling at room temperature, the mixture is added with 2M HCl (25 ml) and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give an oil (1.7 g), which is crystallized from isopropyl ether-hexane to afford the product as a white solid (0.2 g).

Aufarbeitung

temperatureAfter cooling at room temperature
extractionextracted with ethyl acetate
washThe organic phase is washed with 1N HCl
dry with materialwith brine, finally dried
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-a118b428a2f44b9cbf892e93f7e34d88
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08314268B2

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