Chloromethyl Methyl Ether → 5-Bromo-3-methoxy-2-(methoxymethoxy)benzaldehyde

HRID 1907375

Reaktionsgleichung

Reaktionsgleichung von HRID 1907375
C(N(C(C)C)C(C)C)C.[CH3:10][O:11][CH2:12]Cl.[Br:14][C:15]1[CH:16]=[C:17]([O:24][CH3:25])[C:18]([OH:23])=[C:19]([CH:22]=1)[CH:20]=[O:21]>ClCCl>[Br:14][C:15]1[CH:16]=[C:17]([O:24][CH3:25])[C:18]([O:23][CH2:10][O:11][CH3:12])=[C:19]([CH:22]=1)[CH:20]=[O:21]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehyde

Produkt 1

HCID 115653225-Bromo-3-methoxy-2-(methoxymethoxy)benzaldehydeAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyldiisopropylamine (3.01 ml, 17.1 mmol) and methoxymethylchloride (1.5 ml, 15.7 mmol) were added to a dichloromethane solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.3 g, 14.3 mmol) under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→11:9). The purified product was concentrated to dryness under reduced pressure to obtain 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde (4.2 g) as light yellow solid.

Aufarbeitung

  1. washThe reaction solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→11:9)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d9f9d641b30a4b4b934e7049a3b737e3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598162B2

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