Carbon tetrabromide → 2-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene

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Reaction Steps

A mixture of 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol (0.835 g, 4.87 mmol), CBr4 (1.83 g, 5.5 mmol) and PPh3 (1.44 g, 5.5 mmol) in anhydrous CH2Cl2 (10 ml) was stirred for 2 h at room temperature. The solvent was evaporated to dryness and the residue was treated with EtOAc (10 ml) and filtered through a SiO2 bead to give the title compound (1.03 g; 90%), as colourless oil. 1H-NMR (CDCl3) 0.82 (s, 3H); 1.26 (s, 3H); 1.99-2.37 (m, 6H); 2.5 (tr, 2H, J=7.88 Hz); 3.34 (tr, 2H, J=7.27 Hz); 5.31 (broad s, 1H).

Provenance & Evidence