Carbon tetrabromide → 2-(Bromomethyl)-6-methylpyridine

HRID 79350

Reaktionsgleichung

Reaktionsgleichung von HRID 79350
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 707366-Methyl-2-pyridylmethanol

Produkt 1

HCID 125437332-(Bromomethyl)-6-methylpyridineAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice cooled a solution of (6-methylpyridin-2-yl)methanol (400 mg, 3.25 mmol) in dichloromethane (16 mL) under an atmosphere of dry nitrogen was added triphenylphosphine (1278 mg, 4.87 mmol) and carbon tetrabromide (1616 mg, 4.87 mmol). The mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica, eluting with 2-4% methanol in dichloromethane to give 2-(bromomethyl)-6-methylpyridine as an oil (402 mg).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica
  3. washeluting with 2-4% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d5b7f4e6014b4c3e92fe9055a43e9c05
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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