Sodium Carbonate → 3-(pyridin-4-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromopyridine hydrochloride (533.4 mg, 2.7 mmol) in water (4.0 mL) and toluene (4.8 mL) was added slowly a solution of Na2CO3 (714 mg, 6.7 mmol) in water (7.0 mL) at room temperature. The solution was then mixed with 3-formylbenzeneboronic acid (431 mg, 2.9 mmol), Pd(PPh3)4 (100 mg, 0.086 mmol). The reaction mixture was stirred at 85° C. for 24 h, and then cooled to room temperature. The reaction was worked up by extraction of the mixture with CH2Cl2 (4×5 mL). The combined organic phase was dried over anhydrous Na2SO4. The solvent was removed under vacuum, and the residue was purified by a flash chromatography (silica gel, petroleum ether/EtOAc=¼) to give product 10 (420 mg) in 85% yield; 1H NMR (300 MHz, CDCl3): 10.1 (s, 1H), 8.72-8.74 (m, 2H), 8.17 (s, 1H), 7.90-7.99 (m, 2H), 7.69 (t, J=11.4 Hz, 1H), 7.57 (d, J=6.6 Hz, 2H); 13C NMR (75 MHz CDCl3): δ191.5, 150.3, 146.5, 138.8, 136.8, 132.5, 130.1, 129.6, 127.5, 121.3; HRMS (ESI) calcd for C12H9NO (M. Hi) 184.07569; found 184.07538.

Provenance & Evidence