Sodium Bicarbonate → HCID 818845, compound

Participants

Reaction Steps

The compound 3-bromothiophen-2-aldehyde (2) (5.20 g, 27 mmol), solubilized in ethylene glycol dimethyl ether (105 ml) was treated with (Ph3P)4Pd (936 mg, 0.81 mmol), with 2-nitrophenylboronic acid (5 g, 30 mmol) and an aqueous solution of 2M NaHCO3 (70 ml). The reaction mixture was then refluxed for 5 hrs. Then the mixture was cooled to room temperature, the solvent was partially removed under reduced pressure and the resulting mixture was extracted with ethyl acetate (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was chromatographed using 80/20 petroleum ether/ethyl acetate, thus giving the derivative (8) (4.5 g, 83% yield).

Provenance & Evidence