Diiodomethane → 4-Bromo-2-chloro-1-(1-methylcyclopropyl)benzene

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The title compound was synthesized in analogy to 1-bromo-4-(1-methylcyclopropyl)-benzene (described in example S87) using diethyl zinc (2.59 ml, 1M solution in hexane, 2.59 mmol), trifluoroacetic acid (200 μl, 2.59 mmol), CH2I2 (209 μl, 2.59 mmol) and 4-bromo-2-chloro-1-isopropenylbenzene (300 mg, 1.30 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 4-bromo-2-chloro-1-(1-methylcyclopropyl)-benzene (280 mg, 88%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.48 (d, J=2.0 Hz, 1H), 7.30 (dd, J=2.0, 8.5 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 1.32 (s, 3H), 0.81-0.73(m, 4H).

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