1H-Indene, 2-bromo- → 2-Benzyl-1H-indene

Participants

Reaction Conditions

Reaction Steps

A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then quenched by cooling to 0° C. and adding 150 mL of 1.0 M aqueous hydrochloric acid. The organic layer was separated and washed twice with 50 mL of ether. The organic extracts were combined, dried over magnesium sulfate, filtered and the volatiles removed in vacuo to leave a dark oil. The sample was dissolved in a small amount of hexanes and purified by flash column chromatography using silica and hexanes as the elutent. Yield: 1.75 g, 66 percent

Provenance & Evidence