Methyl iodide → 2-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene

HRID 1798057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798057
[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][OH:17].[H-].[Na+].[CH3:20]I>C1COCC1.CCOCC>[Br:1][C:2]1[C:3]([CH2:16][O:17][CH3:20])=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:6][C:7]=1[O:8][CH2:9][O:10][CH3:11]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

Produkt 1

HCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzeneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2-bromo-3,5-bis-methoxymethoxy-phenyl)-methanol (7.68 g, 24.94 mmol) in THF (50 mL) was added NaH at 0° C. The mixture was stirred at room temperature for 20 minutes then MeI (7.84 mL) was added and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with ether (50 mL), filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 70%). 1H NMR (400 MHz, CDCl3δ 6.90 (s, 1H), 6.80 (s, 1H), 6.77 (s, 1H), 5.25 (s, 2H), 5.20 (s, 2H), 4.50 (s, 23.77 (s, 3H), 3.40 (s, 6H).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e3c95b5787a74fe59dc06643bd6ac7e0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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