Sodium Carbonate → HCID 5098321, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 310 mg (1.40 mmol) of methyl 5-bromothiophene-2-carboxylate together with 328 mg (2.10 mmol) of 2-chlorophenylboronic acid were dissolved in 10 ml of dioxane, and 81 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated to 110° C., 1.4 ml (2.80 mmol) of 2 M aqueous sodium carbonate solution were added and the mixture was stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 15:1, then 10:1). This gave 289 mg (61% of theory) of the target compound in a purity of 75%.

Provenance & Evidence