Phosphine, triphenyl-, hydrobromide → 4-Bromo-2-chloro-1-isopropenylbenzene

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Reaction Steps

The title compound was synthesized in analogy to 1-bromo-4-isopropenylbenzene (described in example S87) using triphenylphosphonium bromide (2.32 g, 6.51 mmol), nBuLi (5.09 ml, 1.6M solution in hexane, 8.14 mmol) and 1-(4-bromo-2-chlorophenyl)-ethanone (1.52 g, 6.51 mmol) in DMSO (7 ml). The residue which was isolated was purified by filtration through a short pad of silica using pentane as eluant to give 4-bromo-2-chloro-1-isopropenylbenzene (750 mg, 50%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.51 (d, J=2.0 Hz, 1H), 7.34 (dd, J=2.0, 8.0 Hz, 1H), 7.07 (d, J=8.0 Hz, 1H), 5.24 (m, 1H), 4.96 (m, 1H), 2.07 (m, 3H).

Provenance & Evidence