Pyridine → 1-(Bromomethyl)-4-(tetradecyloxy)benzene

HRID 247930

Reaktionsgleichung

Reaktionsgleichung von HRID 247930
[CH2:1]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]O)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(#N)C.N1C=CC=CC=1.P(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 24614Phosphorus tribromideHCID 100873844-Tetradecyloxybenzyl alcohol

Produkt 1

HCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzeneAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a room temperature slurry of 2.5 g of product from Example 19, 10 ml of acetonitrile and 0.339 g of pyridine is added dropwise, over 3 minutes, 2.11 g of phosphorus tribromide. The reaction is stirred at room temperature for 1 hour, diluted with methylene chloride and concentrated in vacuo. The residue is dissolved in methylene chloride, filtered through a silica gel pad and concentrated in vacuo to give 2.65 g of the desired product as pale yellow crystals.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in methylene chloride
  3. filtrationfiltered through a silica gel pad
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4d4f05d0770d4ec2b0f3bf0f9e2a5dfb
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208247

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