Potassium Iodide → 1,1'-Biphenyl, 2-iodo-

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2-Iodo-1-phenylbenzene was prepared in accordance with the procedure of Heaney and Millar, Org. Syn 40:105 (1960), was used as follows. To a solution of 2-aminobiphenyl (2.53 g, 15.0 mmol) in concentrated hydrochloric acid (3 mL) and water (15 mL) at 0° C. was added sodium nitrite (1.17 g, 17.0 mmol) in water (5 mL). The temperature was held at 0° C. throughout the addition. The resulting brown solution was stirred for 45 min at 0° C., and then poured into potassium iodide (4.9 g, 30.0 mmol) in water (50 mL). The solution was stirred overnight and then extracted with ether (4×). The combined organic layers were washed with 3N hydrochloric acid (3×10 mL) and dried over magnesium sulfate to afford 3.57 g (85%) of the desired compound as a dark purple liquid. IR (neat) 3055.7, 1578.4, 1460.0, 1426.6, 1016.7, 1004.1, 746.9 cm-1 . 1H NMR (300 MHz, CDCl3)δ 7.95 (dd, J=8.1, 1.2 Hz, 1H), 7.34 (m, 7H), 7.03 (tt, J=7.3, 1.9 Hz, 1H). 13C NMR (20 MHz, CDCl3)δ 146.3, 143.9, 139.3, 129.9, 129.1, 128.6, 128.0, 127.8, 127.5, 98.6. Calc'd for C12H9I:279.9749. Found: 279.9739.

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