Zinc chloride-Tetramethylethylenediamine

Zinc(II) chloride-tetramethylethylenediamine complex (4.23 g, 16.7 mmol), 1,10-phenanthroline (101 mg, 0.56 mmol), and benzo[/t]quinoline (1.00 g, 5.6 mmol) are placed in a Schlenk tube. To this mixture a solution of phenylmagnesium bromide (33.5 mL, 1.00 M, 33.5 mmol) in tetrahydrofuran is added dropwise at 0 °C. After stirring for I h, a 0.1-M solution of tris(acetylacetonato)iron in tetrahydrofuran (5.6 mL, 0.56 mmol) and 1,2-dichloro-2-methylpropane (1.42 g, 11.2 mmol) are sequentially added. The reaction mixture is stirred at 0 °C for 16 h and is quenched by the addition of a saturated aqueous solution of sodium bicarbonate (40 mL). After extraction with ethyl acetate (25 mL, 3 times), the organic layer is dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (eluent first hexane to elute the biphenyl, then toluene) to afford 10-phenylbenzo[A]quinoline as a colorless solid mp 90.6-92.5 1.39 g (98%). ... 

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