Methanol → 1-(Bromomethyl)-2-methoxybenzene

HRID 443063

Reaktionsgleichung

Reaktionsgleichung von HRID 443063
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].P(Br)(Br)[Br:12].CO.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:12][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 691542-Methoxybenzyl alcohol

Produkt 1

HCID 403081-(Bromomethyl)-2-methoxybenzeneAusbeute 137,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-hydroxymethyl-2-methoxy-benzene (28.7 g, 0.207 mol) in CH2Cl2 (574 mL) at 0° C. under nitrogen was added slowly PBr3 (13.66 mL, 0.145 mol). After stirring for an additional 1.5 hours, MeOH (13.66 mL) was added and stirred for 5 minutes. To this mixture was added dropwise 10% Na2CO3 (2 mL) solution and stirred for 5 minutes. The mixture was then washed with 10% Na2CO3 (50 mL, 2×) and brine (100 mL). It was dried over MgSO4, and filtered. The filtrate was removed under vacuum to give an oil (40 g) of 1-bromomethyl-2-methoxy-benzene. This material was used without purification.

Aufarbeitung

  1. stirringstirred for 5 minutes
  2. stirringstirred for 5 minutes
  3. washThe mixture was then washed with 10% Na2CO3 (50 mL, 2×) and brine (100 mL)
  4. dry with materialIt was dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f35e4f153c7a4acfb995cadb074ea647
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892039

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