[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[CH:4][CH:3]=14-Bromophenol (5.5 g, 32 mmol) was added to 42 mL of 50% w/w aqueous sodium hydroxide. After stirring for 30 min, 44 mL of toluene was added, followed by 2-chloro-5-nitropyridine (5.0 g, 32 mmol) and tetrabutylammonium bromide (10 g, 32 mmol). After stirring for 1.5 hours at 23° C., the mixture was diluted with 200 mL of water, neutralized with 12M aqueous hydrochloric acid and the mixture was extracted 3× with ether. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo, affording 6 g of 2-(4-bromo-phenoxy)-5-nitro-pyridine. 1H NMR (CDCl3, 500 MHz): 9.05 (d, 1H, J=3.5 Hz), 8.51 (dd, 1H, J=3.5, 9.5 Hz), 7.58 (d, 2H, J=9.0 Hz), 7.08 (m, 3H) ppm. MS (APCl, m/z): 295 [M+H]+.
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