Ethyl Acetate → 1-(3-Bromo-4,5-dimethoxyphenyl)-1-ethanol

HRID 475660

Reaktionsgleichung

Reaktionsgleichung von HRID 475660
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C[Mg+].[Br-].[CH3:17]COC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH3:17])[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 151736561-(3-Bromo-4,5-dimethoxyphenyl)-1-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen, a solution of the 3-bromo-4,5-dimethoxybenzaldehyde (2.45 g; 10 mmol) in dry THF (10 ml) was added via syringe through a septum to a cold (ice-bath) solution of MeMgBr (15 mmol; 5.0 ml of 3.0 M Et2O solution) diluted with 10 ml dry THF. After the addition, the mixture was stirred for 10 minutes at 0° C., then for 1 hour at room temperatures. TLC (Hex:EtOAc=3:1) indicated complete disappearance of the reactant and a new product spot with lower Rf (0.25 vs 0.5).

Aufarbeitung

  1. additionAfter the addition
  2. waitfor 1 hour at room temperatures

Quellen und Nachweise

ORD-Eintrag
ord-0bd70144380943f296bfbc856a7dd3fe
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637575B2

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