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m- And p-iodo-N,N-diethylbenzamides were synthesized from p- and m-iodobenzoyl chlorides with diethylamine in chloroform. The amides were used directly for next step without further purification.
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3 solution was extracted by water (3×50 mL) and concentrated to use directly for next step. tert-Butyl nitrite (10 mL, 1.5 equiv.) was dropped into DMF (30 mL) and the solution was stirred at 65-67 °C, to which 4-tert-butyl-2-bromoaniline (50 mmol) was added carefully. The black solution was stirred at 65 °C for over night. The product was purified by flash chromatography to obtain i-bromo-3-tert-butylbenzene (8.0 g, 75%) as light yellow liquid. The structure was confirmed by GC-MS and NMR.
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