Réaction #660269

Équation de réaction

6-bromobenzo[d][1,3]dioxole-5-carbaldehyde

4-chlorophenylboronic acid

Na2CO3

→

6-(4-chlorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde

Solvants

toluene

methanol

ether

Conditions de réaction

Traitement

1. 1
   Températureat reflux overnight
2. 2
   Lavagewashed with water, brine
3. 3
   Séchagedried over Na2SO4
4. 4
   FiltrationAfter filtration and concentration of the solvent
5. 5
   Lavageeluted with 3% ethyl acetate in hexane
6. 6
   Autreto give the product

Mode opératoire

To a solution of 6-bromobenzo[d][1,3]dioxole-5-carbaldehyde (4.6 g), 4-chlorophenylboronic acid (3.78 g) and tetrakis(triphenylphosphine)palladium(0) (0.232 g) in toluene (80 mL) and methanol (30 mL) was added 2N aqueous Na2CO3 (30 mL). The mixture was stirred at reflux overnight. The mixture was diluted with ether (400 mL) and washed with water, brine and dried over Na2SO4. After filtration and concentration of the solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give the product.

Source