Hydrochloric Acid → 2-Chloro-3-fluoro-4-methoxybenzaldehyde

HRID 1945104Notizen

Reaktionsgleichung

[Cl:1][C:2]1[C:3]([F:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN([CH:19]=[O:20])C.Cl>C1COCC1.CCCCCC>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][C:7]=1[CH:19]=[O:20]

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF are cooled to −70° C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After one hour at −70° 3.93 ml DMF in 7 ml THF are added at −70° C. and the mixture is stirred another hour at −70° C. 15 ml of a 1 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); δ=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

Aufarbeitung

temperaturethe reaction is warmed to ambient temperature over 18 hours
customThe reaction mixture is partitioned between diethyl ether and water
extractionThe aqueous phase is extracted with diethyl ether
washthe combined organic phases are washed with brine
dry with materialdried over sodium sulfate
customevaporated
customThe crude product is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-6798d3e44494468587952719ff4efde8
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08394958B2

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