[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:8]([C:11]1[CH:12]=[CH:13][C:14](Cl)=[N:15][CH:16]=1)([O-:10])=[O:9].C(OCC)C>[OH-].[Na+].C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:15][CH:16]=1)([O-:10])=[O:9]
Phenol (0.9 g, 9.5 mmol) was dissolved in sodium hydroxide (50% solution, 12 mL). 5-Nitro-2-chloropyridine (1.5 g, 9.5 mmol) in toluene (15 mL) was added followed by addition of tetra-butylammonium bromide (0.3 g, 0.95 mmol). The reaction mixture was stirred for 16 hours at 20° C. and 5 hours at 80° C. where after it was cooled to room temperature and diethyl ether (100 mL) added. The organic phase was washed with water (5×50 mL), dried (MgSO4), and concentrated in vacuo to give 1.0 g of 5-nitro-2-phenoxypyridine.
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