Allyltributylstannane → 4-Allyl-3-methoxybenzonitrile

HRID 1519593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519593
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[Li+].[Cl-]>C1(C)C=CC=CC=1>[CH2:14]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11])[CH:13]=[CH2:12]

Komponenten

5

Edukt 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 225911814-Bromo-3-methoxybenzonitrile

Produkt 1

HCID 675133484-Allyl-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-3-methoxybenzonitrile (1.4 g, 6.7 mmol), allyl-tributyl-stannane (2.7 g, 8.1 mmol), LiCl (0.86 mg, 20 mmol) and Pd(PPh)4 (0.2 g) in 25 mL of anhydrous toluene was refluxed under N2 overnight. Checked the reaction with TLC and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 4-allyl-3-methoxybenzonitrile. MS m/z: 174 (M+1)+.

Aufarbeitung

  1. temperaturewas refluxed under N2 overnight
  2. customChecked the reaction with TLC
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-471152da6fcf4871bc1fe388b8187691
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073882B2

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