2-Chloroaniline → 1,4-Dimethoxy-9H-carbazole

HRID 1752217

Reaktionsgleichung

CC([O-])(C)C.[Na+].Cl[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:25][O:24][C:17]1[C:16]2[NH:10][C:9]3[C:8](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:21]=2[C:20]([O:22][CH3:23])=[CH:19][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 170 °C

Versuchsvorschrift

Following a published procedure (Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403-9410), NaOtBu (0.754 g, 7.84 mmol), Pd(OAc)2 (0.014 g, 0.06 mmol), and [HPtBu3][BF4] (0.023 g, 0.078 mmol) were suspended in dry toluene (5 mL) in a microwave vial. 2-Chloroaniline (0.165 mL, 1.567 mmol) and 2-bromo-1,4-dimethoxybenzene (0.240 mL, 1.598 mmol) were then added, and the vial was sealed. The reaction was then heated in the microwave reactor at 170° C. for 4 h, allowed to cool, and then quenched by addition of 1M HCl. The aqueous phase was extracted with CH2Cl2, the organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane) to afford the title product (0.193 g, 55%).

Aufarbeitung

customthe vial was sealed
temperatureto cool
customquenched by addition of 1M HCl
extractionThe aqueous phase was extracted with CH2Cl2
dry with materialthe organic layer was dried over Na2SO4
filtrationfiltered
customcondensed
customThe crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag: ord-ac1c7dee59534fefb9bcc2c5e62e4deb
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09162980B2

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