Diiodomethane → 1-Bromo-4-(1-ethylcyclopropyl)-benzene

Participants

Reaction Steps

The title compound was synthesized in analogy to 1-bromo-4-(1-methoxycyclopropyl)-benzene (described in example S89) using 2,4,6-trichlorophenol (580 mg, 2.94 mmol), diethyl zinc (2.94 ml, 1M solution in hexane, 2.94 mmol), CH2I2 (237 μl, 2.94 mmol) and 1-bromo-4-(1-methylenepropyl)-benzene (310 mg, 1.47 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 1-bromo-4-(1-ethylcyclopropyl)-benzene (280 mg, 85%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.39 (d, J=8.5 Hz, 2H), 7.16 (d, J=8.5 Hz, 2H), 1.55 (q, J=7.5 Hz, 2H), 0.82 (t, J=7.5 Hz, 3H), 0.75-0.71(m, 2H), 0.68-0.64 (m, 2H).

Provenance & Evidence