Reacción #70965

Ecuación de reacción

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

Na2CO3

2-formylphenylboronic acid

→

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

Disolventes

dimethoxy-ethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente