Sodium Carbonate → 6-Phenylpyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Phenylboronic acid (1.46 g, 12 mmol) and Na2CO3 (2.65 g, 25 mmol) were dissolved in 60 mL of degassed 4:1H2O/MeOH. This solution was added via cannula to a solution of 1.86 g (10 mmol) of 2-bromo-6-formylpyridine and 116 mg (0.10 mmol) of Pd(PPh3)4 in 50 mL of degassed toluene. The biphasic mixture was vigorously stirred and heated at 70° C. under N2 for 4 h. On cooling to RT, the organic phase was separated and the aqueous phase was washed with 3×25 mL of Et2O. The combined organic extracts were washed with 3×25 mL of H2O and 20 mL of brine and dried over Na2SO4. After removing the volatiles in vacuo, the resultant brown oil was chromatographed on silica with hexanes/CH2Cl2. Clean fractions were combined and the volatiles were removed to provide 2-formyl-6-phenylpyridine as a white solid.

Provenance & Evidence