Toluene → 5-Nitro-2-phenylpyridine

Participants

Reaction Steps

A mixture of toluene (15 mL) and water (5 mL) was degassed with argon for 5 minutes. Sodium carbonate (0.80 g, 4.54 mmol) was added and the mixture was degassed with argon gas for 5 minutes. Phenyl boronic acid (0.59 g, 4.54 mmol) and 2-chloro-5-nitro-pyridine (0.6 g, 3.78 mmol) were added and the mixture was again degassed with argon gas for 5 minutes. Tetrakis palladium triphenyl phosphine (0.88 g, 0.76 mmol) was added and the mixture was degassed with argon gas for 5 minutes. The resulting mixture was heated to reflux for 3 hours. The mixture was then diluted with ethyl acetate, washed with water then brine solution. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford a residue which was purified by column chromatography using silica gel 60-120 mesh (5% ethyl acetate in hexane) to afford 0.5 g (66%) of 5-nitro-2-phenyl-pyridine. LCMS purity: 201 (M+1)+, 98.2%, 1H NMR (DMSO-d6): δ 9.5 (s, 1H), 8.55 (dd, 1H), 8.1 (m, 2H), 7.9 (d, 1H), 7.55 (m, 3H).

Provenance & Evidence