Indene → 1-bromo-2-(3-indenyl)ethane

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Reaction Steps

A 1.6 M n-BuLi solution in hexane (100 mL, 0.16 mol) was added at 0° C. to a solution of indene (18.6 g, MW=116.16, 0.16 mol) in 300 mL of ether. The resulting suspension was allowed to warm to room temperature and stirred for 4 h at the same temperature. Then the indenyl lithium suspension was cooled again to −50° C. and added of a solution of 1,2-dibromoethane (0.24 mol, 21 mL) in 50 mL of ether. The reaction mixture was allowed to warm up slowly to room temperature and stirred overnight. Then it was treated with a saturated aqueous solution of NH4Cl. The organic phase was isolated, evaporated off to dryness and distilled in vacuo, b.p. 110° C./0.5 torr. Yield 21.6 g (60%). The title compound was characterized by NMR spectroscopy.

Provenance & Evidence