1-Bromo-2,2-dimethylpropane → 4-(2,2-Dimethylpropyl)4-ethenylbenzene

Participants

Reaction Steps

To a solution of 0.8 g (33.10 mmol) of magnesium turnings and 2.0 g (13.2 mmol) of 1-bromo-2,2-dimethylpropane in 10 mL diethyl ether was added a solution of 1.42 g (7.76 mmol) of 4-bromostyrene and 69 mg (0.13 mmol) of Ni(dppf)Cl2 The resulting reaction mixture was heated at refluc for 8 h. The reaction was quenched with 50% saturated NH4Cl, and was extracted with MTBE (2×150 mL). The combined extractions were washed with water, dried and concentrated. Flash chromatography on a Biotage 40M cartridge with hexanes as the eluant afforded 1.74 g of the title compound: 1H NMR (500 Mhz) δ 0.93 (s, 9H), 2.49 (s, 2H), 5.20 (d, J=10.9, 1H), 5.73 (d, J=17.6, 1H), 6.72 (dd, J1=17.6, J2=10.8, 1H), 7.10 (d, J=8.2, 2H), 7.33 (d, J=8.0, 2H); ESI-MS 161 (M+H); LC-1: 4.4 min.

Provenance & Evidence