Sodium Bromide → 4-Bromo-3-iodotoluene

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To a mixture of 2-iodo-4-methylaniline (50 g, 214.55 mmol) in HOAc (250 mL), H2SO4 (10 mL), and H2O (40 mL) was added a solution of NaNO2 (14.5 g) in H2O (80 mL) at 0° C. The solution was stirred for 1.5 h. This was defined as mixture A. In another round bottom flask, a mixture of NaBr (107 g), CuSO4 (32.2 g), Cu (38.9 g), H2SO4 (39 mL), and H2O (25 mL) was refluxed for 1.5 h. To this mixture was added mixture A, and the solution was then refluxed for 3 h. The solution was treated with water and extracted with EA (500 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and then concentrated in vacuo. Purification by column chromatography over silica gel eluted with PE afforded the product as colorless oil (43 g, yield 68%). 1H NMR (300 MHz, CDCl3): δ 7.69 (m, 1H), 7.47 (d, J=8.1 Hz, 1H), 7.00 (m, 1H), 2.26 (s, 3H) ppm.

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