Sodium Carbonate → HCID 67296304, compound

Participants

Reaction Conditions

Reaction Steps

{4-[(2-Ethoxy-2-oxoethyl)thio]phenyl}boric acid 2.80 g (11.7 mmol) and 3-bromo-2-cyclopenten-1-one 1.88 g (11.7 mmol) synthesized according to the method of C. M. Marson et al. were dissolved in 25 mL of 1,2-dimethoxyethane, followed by addition of 12 mL of 3N aqueous sodium carbonate solution and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) methylene chloride complex 0.48 g (0.59 mmol), and the mixture was stirred for 4 hours at 90° C. The temperature of the reaction solution was adjusted to room temperature, followed by concentration. Then, water was added to the residue, followed by extraction with methylene chloride and drying over anhydrous magnesium sulfate. The solvent was concentrated, and the crude product obtained was purified by silica gel column chromatography (Biotage, solvent for elution; hexane/ethyl acetate) to give the title compound 2.43 g (yield 75%).

Provenance & Evidence