[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[CH:18]([Br:21])(Br)Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Br:21][C:18]1[CH:7]=[N:8][C:9]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=26-Fluoroindole (500 mg, 3.70 mmol) was combined with benzyltriethylammonium chloride (44.4 mg, 0.185 mmol) and toluene (0.32 mL) was added. Bromoform (0.342 mL, 3.70 mmol) was added and the temperature was brought to 40° C. A solution of NaOH (1.110 g, 7.50 mmol) in water (2.22 mL) was then added over 15 minutes. This caused a very dark color to form. The reaction was stirred as a biphasic mixture at 40° C. for 16 h before cooling and partitioning between ethyl acetate and water. The separated aqueous layer was extracted with ethyl acetate and the combined organics dried over MgSO4. Purification by silica gel flash chromatography (ethyl acetate/heptane) gave 3-bromo-7-fluoro-quinoline (171.9 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.93 (d, J=2.1 Hz, 1H) 8.33 (d, J=2.0 Hz, 1H) 7.68-7.82 (m, 2H) 7.39 (td, J=8.6, 2.5 Hz, 1H); MS (M+1): 226.0.
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