Phosphonium, (bromomethyl)triphenyl-, bromide (1:1) → (Z)-2-(2-bromovinyl)-6-fluoroquinoline

HRID 920896

Reaktionsgleichung

Reaktionsgleichung von HRID 920896
[Br-].[Br:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[C:35]([CH:40]=O)[CH:34]=[CH:33]2>C1COCC1>[Br:2]/[CH:3]=[CH:40]\[C:35]1[CH:34]=[CH:33][C:32]2[C:37](=[CH:38][CH:39]=[C:30]([F:29])[CH:31]=2)[N:36]=1

Komponenten

5

Edukt 3

HCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 31596056-Fluoroquinoline-2-carbaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86683113(Z)-2-(2-bromovinyl)-6-fluoroquinolineAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To as suspension of (bromomethyl)triphenylphosphonium bromide (14.94 g, 34.3 mmol) in 100 mL of THF was added potassium tert-butoxide (3.84 g, 34.3 mmol) portionwise under Ar. Then the reaction mixture was stirred for 1 h at this temperature. 6-Fluoroquinoline-2-carbaldehyde (5 g, 28.5 mmol) in 40 mL of THF was added. The resulting reaction mixture was stirred for 5 h at −75° C. and allowed to warm up overnight. The reaction mixture was diluted with petrol ether and the solid was sucked off. The mother liquid was concentrated, diisopropyl ether was added and the formed precipitate was sucked off. The mother liquid was purified by column chromatography (cyclohexane/EA) to give 4.7 g (65.3%) of the title compound as brown solid. LC-MS: m/e 254.0.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 5 h at −75° C.
  3. temperatureto warm up overnight
  4. concentrationThe mother liquid was concentrated
  5. additiondiisopropyl ether was added
  6. customThe mother liquid was purified by column chromatography (cyclohexane/EA)

Quellen und Nachweise

ORD-Eintrag
ord-20c5ec6bafca4fb0a9ce6892d8c2c734
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273068B2

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