Pyridine → 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

HRID 2393581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393581
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5]O.N1C=CC=CC=1.S(Cl)([Cl:22])=O>CCOCC>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][Cl:22]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 101927773-Bromo-2,5-dimethoxybenzyl Alcohol

Produkt 1

HCID 103081541-Bromo-3-chloromethyl-2,5-dimethoxy-benzeneAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 8.18 gm (33.11 mmol) of 3-bromo-2,5-dimethoxybenzyl alcohol and 0.8 ml pyridine in 100 ml ether was added dropwise a solution of 8.5 ml (116 mmol) thionyl chloride in 20 ml ether. After stirring at ambient temperature for 20 hours, the reaction mixture was poured onto ice. The ether extract was washed with brine, dried (NaSO4), filtered and concentrated in vacuo to give 7.59 gm of a colorless oil. A portion, 3.9 gm, was purified by silica gel chromatography using 3:7 CH2 Cl2 :hexane to yield 3.62 gm of a white solid.

Aufarbeitung

  1. additionthe reaction mixture was poured onto ice
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62cfc9a089764bcdb5a83111f341356a
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807897

Notizen zur Reaktion

Wird geladen…