Cesium carbonate → 2-(Biphenyl-4-ylmethoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-chlorobiphenyl (15 mg, 79.5 μmol) and 1,4-dioxane (1.5 ml) were added water (0.15 ml), cesium carbonate (117 mg, 358 μmol), sodium (2-hydroxyethoxy)methyl trifluoroborate (19.7 mg, 119 mol), palladium (II) acetate (5.37 mg, 23.9 μmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (19.6 mg, 47.7 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 13 hours. After the reaction mixture was cooled at room temperature, water and dichloromethane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 NH silica gel) to obtain the title compound (6.8 mg, 30 μmol, 38%).

Provenance & Evidence