Synthesis
0.5mmol of 2-(2-chloro-6-nitrophenoxy)pyridine and 0.08ml of methyl trifluoromethanesulfonate were dissolved in 20ml of toluene and reacted at 100°C for 2 hours in a three-necked flask under nitrogen protection. The solvent was removed, 10mmol of sodium metal and 20ml of methanol were added, and the reaction was carried out at 80°C for 30min under nitrogen protection. After the reaction was completed by TLC detection, ethyl acetate was extracted, the extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. 2-chloro-6-nitrophenol (89% yield) was separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 6:1).
References
[1] Chinese Chemical Letters, 2010, vol. 21, # 4, p. 403 - 406
[2] Synthetic Communications, 2011, vol. 41, # 20, p. 2985 - 2992
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3435 - 3450
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525
[5] Journal of the Chemical Society, 1927, p. 1692
