3-Bromo-4-hydroxybenzaldehyde → 3-Bromo-4-((4-methoxybenzyl)oxy)benzaldehyde

HRID 68614

Reaktionsgleichung

Reaktionsgleichung von HRID 68614
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[Br:1])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 763083-Bromo-4-hydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 1650214-Methoxybenzyl bromide

Produkt 1

HCID 230102233-Bromo-4-((4-methoxybenzyl)oxy)benzaldehydeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-bromo-4-hydroxybenzaldehyde (5.0 g, 24.9 mmol; 1 eq) in DCM (10 mL), was added 1-(bromomethyl)-4-methoxybenzene (6.0 g, 29.88 mmol, 1.2 eq, Aldrich, Milwaukee, Wis., USA) and DIEA (8.7 mL, 49.7 mmol, 2 eq). After stirring at room temperature for 18 h, the reaction mixture was diluted with DCM and washed with saturated NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 8.0 g of 4-(4-methoxybenzyloxy)-3-bromobenzaldehyde (32).

Aufarbeitung

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-095c940df06246f88c3e22d39134361a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822467B2

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