3-Phenoxypyridine

General procedure: To a stirred suspension of appropriate aryl halide(2.0 mmol) and phenol (2.0 mmol) in 6 ml water, Ni-alumina (0.125g, 6 mol percent ofnickel metal) was added followed by KGeneral procedure: A solution of the appropriate arylboronic acid (1.0 mmol), the diphenyliodonium trifluoromethanesulfonate (1.2 mmol), eosin Y (34.5 mg, 0.02 mmol) and t-BuONa (1.1 mmol, 25 mg) in DMF (2.0 mL) in a borosilicate flask was subjected to constant irradiation with an LED 18-watt visible light, and the reaction was stirred at room temperature for 1–2 h. After completion of the reaction (TLC), the reaction mixture was poured into H2O (50 mL) and stirred for another 2 h. The aqueous phase was extracted with CH2Cl2(2 × 20 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The residues was purified by silica gel column chromatography [ethyl acetate – petroleum ether (60–90 °C) = 1:10–1:4] to afford the pure product. 3-Phenoxypyridine (3h): slightly yellow oil; 1H NMR (CDCl3, 400 MHz) δ 8.21–8.20 (m, 1H), 7.70–7.66 (m, 1H), 7.42–7.38 (m, 2H), 7.16–7.14 (m, 2H), 7.01–6.97 (m, 1H), 6.91–6.89 (m, 1H); 13C NMR (CDCl3, 125 MHz) δ 163.8, 154.2, 147.8, 139.4, 129.7, 124.6, 121.2, 118.4, 111.5.Pyridin-3-ol (9.5 g, 100 mmol) and potassium hydroxide (5. 6 g, 100 mmol) were heated at 150°C for 30 minutes. An excess of pyridin-3-ol (6 g, 63 mmol) was then added together with bromo-benzene (15.7 g, 100 mmol) and copper powder (0.2 g, 3 mmol). The resulting mixture was then heated at 200°C overnight. The copper powder was filtered off, and the resulting mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give a solid. This solid was washed with diethyl ether and the filtrate collected and concentrated in vacuo. The resulting product was purified by column chromatography using a lOg silica gel column, eluting with 20percent ethyl acetate: heptane and gave 3-phenoxy-pyridine (1. 15g, 7percent).

Molecular Weight:171.19
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:171.068413911
Monoisotopic Mass:171.068413911
Topological Polar Surface Area:22.1
Heavy Atom Count:13
Complexity:143
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes