Sodium Bicarbonate → 6-(Benzyloxy)-2-(2,6-dichlorophenyl)quinoline

Participants

Reaction Steps

To a solution of 3 g of 6-(benzyloxy)-2-chloroquinoline 12 in toluene (294 ml) is added Pd(PPh3)4 (1 g). After 30 minutes, a solution of 2,6-dichlorophenylboronic acid (4.22 g) in methanol (186 ml) and 120 ml of a saturated aqueous solution of NaHCO3 is added. The reaction is heated under reflux for 4 h. After evaporation, the aqueous phase is extracted with AcOEt (3×20 ml). The organic phases are washed with brine, dried over MgSO4 and evaporated to dryness. The residue is purified over silica gel using AcOEt/petroleum ether 5/95 then 10/90 as eluent to give 6-(benzyloxy)-2-(2,6-dichlorophenyl)quinoline 19 as an oil.

Provenance & Evidence