Chloromethyl Methyl Ether → 1-Bromo-3-[(methoxymethoxy)methyl]benzene

HRID 78263

Reaktionsgleichung

Reaktionsgleichung von HRID 78263
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[H-].[Na+].[CH3:12][O:13][CH2:14]Cl>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][O:6][CH2:12][O:13][CH3:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 851413-Bromobenzyl alcohol

Produkt 1

HCID 114475781-Bromo-3-[(methoxymethoxy)methyl]benzeneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a tetrahydrofuran (100 mL) solution of 3-bromobenzyl alcohol (10 g, 54 mmol) was added sodium hydride (2.3 g, 98 mmol, 60% in oil) at room temperature. Then, chloromethyl methyl ether (5.2 g, 64 mmol) was added to this suspension, which was stirred for 15 minutes at 60° C. This mixture was partitioned into ethyl acetate and water. The organic layer was separated and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1) to obtain the title compound (10 g, 83%).

Aufarbeitung

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-4203a6b99c9c41c7b61a2107c2ecb1da
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

Verknüpfte Notizen

Wird geladen…