Synthesis of substituted phenyl 2-pyridyl ethers was written by Acharya, S. P.;Nargund, K.S.. And the article was included in Journal of Scientific and Industrial Research, Section B: Physical Sciences in 1962.COA of Formula: C11H9NO This article mentions the following:
Method A to 0.011 mole KOH in EtOH was added 0.011 mole 2,4-Cl(O2N)C6H3OH, the whole refluxed 0.33 hr., 0.011 mole 2,5-Cl(O2N)C5H3N (I) added, refluxed 2-3 hrs., the whole steam distilled, and the non-volatile residue washed with 5% NaOH gave 64% 2,4-Cl(O2N)C6H3OC5H3NNO2-5′ (II), m. 128-9°. Method B 2,6,4-Cl2(O2N)C6H2OH and I, 0.011 mole each, in 10-15 ml. MeCH(OH)CH2OH and a trace of Cu bronze was heated 3 hrs. at 130-40°, the whole poured into H2O, and the solid filtered off, washed with 5% NaOH, and steam distilled to give 56% 2,6,4-Cl2(O2N)C6H2OC5H3NNO2-5′ (III), m. 153-4°. To 0.005 mole II, 5 g. NH4Cl, 10 ml. H2O, and 20 ml. EtOH at 70-80° was added 3 g. reduced Fe, portionwise; the whole stirred 0.75 hr. at 70-80°, filtered, and the filtrate concentrated gave 69% 4,5′-diamino derivative, m. 174-5°; di-N-acetyl derivative m. 147-8°. The following substituted phenyl 2-pyridyl ethers were prepared (substituents in pyridine ring, substituents in benzene ring, method of preparation, % yield, m.p., m.p. of 4,5′-diamino derivative, m.p. of di-N-acetyl derivative given): 5′-O2N, 3,4-Cl(O2N), A, 61, 119-20°, 145-6°, 195-6°; 5′-O2N, 2,5,4-Cl2(O2N), A, 52, 151-2°, –, –; 5′-O2N, 2,6,4-Cl2(O2N), Bgr, 56, 153-4°, 147-8°, 226-7°; 3,5′-Cl(O2N), 2,4-Cl(O2N), A, 50, 109-10°, 164-5°, 171-2°; 3′,5′-Cl(O2N), 3,4-Cl(O2N), A, 57, 104-5°, –, –; 3′,5′-Cl(O2N), 2,5,4-Cl2(O2N), B, 56, 127-30°, –, –; and 3′,5′-Cl(O2N), 2,6,4-Cl2(O2N), B, 141-2°, 54, 215-16°, 252-3°. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0COA of Formula: C11H9NO).
2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.COA of Formula: C11H9NO