2-Quinolinecarboxaldehyde → (Z)-2-(2-Bromovinyl)quinoline

HRID 920895

Reaktionsgleichung

[Br-].[Br:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH:39]=O>C1COCC1>[Br:2]/[CH:3]=[CH:39]\[C:30]1[CH:31]=[CH:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:29]=1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

A suspension of 24.97 g (57.3 mmol) of (bromomethyl)triphenylphosphonium bromide in 160 mL of THF was chilled to −70° C. under argon. Then, 6.43 g (57.3 mmol) of potassium tert-butoxide were added portionwise and the suspension was allowed to stir at this temperature for 1 h. A solution of 7.5 g of (47.7 mmol) quinoline-2-carbaldehyde in 40 mL of THF was slowly added dropwise. The mixture was allowed to stir at −75° C. for further 5 hours and then warmed to room temperature overnight. 160 mL of PE were added. The precipitate formed was sucked off. The mother liquid was evaporated and the residue was stirred with diisopropyl ether. The residue formed was sucked off. Purification by chromatography (heptane/EA 3/1) yielded 6.6 g (59.1%) of the title compound.

Aufarbeitung

stirringto stir at −75° C. for further 5 hours
temperaturewarmed to room temperature overnight
addition160 mL of PE were added
customThe precipitate formed
customThe mother liquid was evaporated
stirringthe residue was stirred with diisopropyl ether
customThe residue formed
customPurification by chromatography (heptane/EA 3/1)

Quellen und Nachweise

ORD-Eintrag: ord-610107384e8d4a35a8698cd063865337
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09273068B2

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