Potassium Carbonate → 5-Phenyl-2-furaldehyde

Participants

Reaction Steps

A solution of 5-bromo-furan-2-carbaldehyde (1.08 g, 6.16 mmol, 1 eq), phenylboronic acid (0.90 g, 7.39 mmol, 1.1 eq), tetrabutylammonium bromide (1.99 g, 6.16 mmol, 1 eq), palladium acetate (30 mg, 0.0.12 mmol 0.02 eq), K2CO3 (2.13 g, 15.4 mmol, 2.5 eq) in water (10 mL) is stirred under nitrogen at room temperature overnight. Upon completion, the reaction mixture turns into a black mass floating in the solution. The reaction is diluted with 40 ML water and extracted with EtOAc (3×100 mL). The organic layers are combined and stirred with charcoal for 30 min, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give an oil. The product is purified by silica gel chromatography using a Biotage Flash 40M column (10% EtOAc/heptane). Yield 70.1%. HRMS (FAB) calculated for C11H8O2+H 173.0603, found 173.0607.

Provenance & Evidence