1,3-Dibromopropane → 4-(3-Bromopropoxy)-3-methoxybenzonitrile

HRID 233159

Reaktionsgleichung

Reaktionsgleichung von HRID 233159
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>C(#N)C>[Br:18][CH2:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11]

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 781354-Hydroxy-3-methoxybenzonitrile

Produkt 1

HCID 104232304-(3-Bromopropoxy)-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmol), K2CO3 (12.5 g), and 1,3-dibromopropane (15 g, 75 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours and left standing at room temperature overnight. The solvent of the reaction was removed on a rotary evaporator, and the crude solid was extracted into methylene chloride (500 ml). The insolubles were filtered off. The dichloromethane solution was concentrated and the material was purified on a flash chromatography column (SiO2, 105 g; eluted with 2:3 dichloromethane:hexane, and then with dichloromethane). The desired product thus purified weighed 7.74 g (52%). Recrystallization twice from ethanol gave analytically pure 4-(3-bromopropoxy)-3-methoxybenzonitrile, m.p.=99°-101° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. waitleft
  4. customThe solvent of the reaction was removed on a rotary evaporator
  5. extractionthe crude solid was extracted into methylene chloride (500 ml)
  6. filtrationThe insolubles were filtered off
  7. concentrationThe dichloromethane solution was concentrated
  8. customthe material was purified on a flash chromatography column (SiO2, 105 g
  9. washeluted with 2:3 dichloromethane
  10. customThe desired product thus purified
  11. customRecrystallization twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-749295db04754efa9e54f560e8c494be
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591745

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