Water → HCID 22173111, Verbindung

HRID 2298470Notizen

Reaktionsgleichung

Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

2.5 g (13.8 mmol) of 7-chloro-2-methyl-1-indanone (1), 2.86 g (16.6 mmol) of naphthylboronic acid, 0.22 g (0.68 mmol) of tetrabutylammonium bromide and 3.66 g (34.6 mmol) of sodium carbonate were placed in 40 ml of o-xylene in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 1.55 mg (0.0069 mmol) of palladium acetate and 7.3 mg (0.027 mmol) of triphenylphosphine, the reaction mixture was stirred for 9 hours at 125° C. After addition of 40 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 40 ml each time of ether, the combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 3.38 g of (16) as solid.

Aufarbeitung

customthe mixture was degassed a number of times
customthe phases were separated
extractionthe aqueous phase was extracted 3 times with 40 ml each time of ether
washthe combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag: ord-6ddf955ea9b942268bf255ef1e022bf7
Quelldatensatz: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06492539B1

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