Sodium Carbonate → HCID 21196371, compound

Participants

Reaction Steps

A mixture of 5-bromo-2-methoxybenzaldehyde (10.00 g, 1.82 mmol) and tetrakis (triphenylphosphine)palladium (O) (2.10 g, 1.82 mmol, 3.9 mol %) in DME (filtered through Al2O3) (50 ml) was stirred at RT for 0.25 h. Sodium carbonate (2M, 50 ml, 0.10 mol %) and diethyl (3-pyridyl)borane (6.817 g, 46.36 mmol) were added, the mixture heated to reflux for 5.5 h then allowed to stand at RT overnight. The dark brown reaction mixture was partitioned between water (50 ml) and Et2O (100 ml) and the organic layer separated and combined with two further Et2O extracts (1×50 ml, 1×25 ml). The organic phase was extracted with 2N hydrochloric acid (2×50 ml) then the aqueous extract was basified with 3M NaOH and extracted with Et2O (1×150 ml, 2×50 ml). The combined organic extract was washed with brine (50 ml), dried (Na2SO4), concentrated in vacuo then submitted to column chromatography [SiO2; Et2O] to furnish the title compound (3.318 g) as a pale yellow solid (Found: C, 73.40; H, 5.20; N, 6.44. C13H11NO2 requires C, 73.23; H, 5.20; N, 6.57%.).

Provenance & Evidence