Potassium Iodide → 2-Bromo-9,9-didecyl-7-iodo-9H-fluorene

Participants

Reaction Steps

To a mechanically stirred mixture of 7-iodo-2-bromofluorene (example 2; 41.34 g, 0.1 114 mol), DMSO (100 mL), potassium iodide (1.79 g), and powdered potassium hydroxide (28 g) cooled in a cold water bath, 1-bromodecane (53 mL) was added dropwise, and the mixture was stirred for 24 hours. The oil that separated on dilution with water, was extracted with toluene. Toluene extract was washed with water, dried and concentrated. The residual oil was passed through a column of 300 g alumina. Elution with 900 mL hexanes gave the product as an oil, 65 g. This was left in 200 mL of isopropanola when the product solidified, 58.63 g (81% yield), m.p. 43-45° C. Mass Spec. (m/z): 698 (M+ diiodo), 650, 652 (M+).

Provenance & Evidence