1-Bromo-2,4-dimethoxybenzene → HCID 44610346, Verbindung

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Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1Br.C([Li])CCC.[I-].[CH3:18][N+:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>C(OCC)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:24]1[CH:23]=[C:22]([CH3:25])[CH:21]=[CH:20][N:19]1[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a stirred solution of 2,4-dimethoxybromobenzene (1) (0.5 g, 2.3 mmol) in diethyl ether (10 ml) cooled at −78° C. under nitrogen was added a solution of n-butyl lithium (1.0 ml, 2.5 mmol of 2.5M solution in hexane) drop wise. The mixture was stirred at −78° C. for 2 hours and then 1,4-dimethylpyridinium iodide (2) (0.54 g, 2.5 mmol) was added as a solid. The resultant mixture was allowed to warm to room temperature and stirred at room temperature for 18 hours. The mixture was diluted with water (20 ml) and extracted with diethyl ether (2×15 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated to yield 2-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2-dihydropyridine (4) (0.5 g, 93%) as a brown oil, 1H NMR CDCl3 ??1.7 (s, 3H), 2.7 (s, 3H), 3.8 (s, 6H), 4.45 (dd, 1H, J=2,7) 4.85 (m, 1H), 5.4 (d, 1H, J=4), 6.05 (d, 1H, J=7), 6.45 (d, 1H, J=3), 6.55 (m, 1H), 7.5 (d, 1H, J=9).

Aufarbeitung

temperatureto warm to room temperature
stirringstirred at room temperature for 18 hours
extractionextracted with diethyl ether (2×15 ml)
dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-47574f91a201429caef94b18b75e4f76
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07718830B2

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