Fluorene → 2-Bromo-9H-fluorene

Participants

Reaction Steps

To a solution of fluorene (16.6 g, 0.1 mol), in propylene carbonate (125 mL), at 60° C., N-bromosuccinimide (17.8 g, 0.1 mol) was added in one portion, and the mixture was allowed to cool over a period of 1 hour. The solids separated on dilution with water (2 L), were collected, dissolved in toluene (250 mL), and the toluene solution was washed with water. The solids left after concentration were recrystallized from ethanol-water, 23.3 g (95% yield), m.p. 95.6-101.3° C. Mass Spec. (m/z):322, 324, 326 (M+ dibromo), 244, 246 (M+).

Provenance & Evidence