Reaktion #70965

Reaktionsgleichung

5-bromo-1,3-benzodioxole-4-carbaldehyde

Na2CO3

2-formylphenylboronic acid

→

5-(2-Formylphenyl)-1,3-benzodioxole-4-carbaldehyde

Lösungsmittel

dimethoxy-ethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturunder reflux until the starting material
3. 3
   Sonstigewas consumed (monitored by TLC)
4. 4
   workup.ADDITIONThen the mixture was poured onto ice-water (30 ml)
5. 5
   Extraktionthe aqueous phase was extracted with dichloromethane (3×30 ml)
6. 6
   TrocknenThe combined organic phases were dried over anhydrous MgSO4
7. 7
   SonstigeThe solvent was evaporated in vacuo
8. 8
   Sonstigethe crude product was purified by column chromatography with a mixture of hexane:ethyl acetate (9:1) as the eluent

Vorschrift

To a solution of 5-bromo-1,3-benzodioxole-4-carbaldehyde (0.458 g, 2.00 mmol) in dry dimethoxy-ethane were added Pd(PPh3)4 (5 mol %, 0.10 mmol), 2.5 ml 2M Na2CO3 and 2-formylphenylboronic acid (0.450 g, 3.00 mmol) under argon. The reaction mixture was heated under reflux until the starting material was consumed (monitored by TLC). Then the mixture was poured onto ice-water (30 ml) and the aqueous phase was extracted with dichloromethane (3×30 ml). The combined organic phases were dried over anhydrous MgSO4. The solvent was evaporated in vacuo and the crude product was purified by column chromatography with a mixture of hexane:ethyl acetate (9:1) as the eluent.

Quelle