Carbon tetrabromide → 5-(2-Bromoethyl)benzofurazan

Participants

Reaction Steps

A solution of 5-(2-hydroxyethyl)benzofurazan (1.0 g, 6.1 nmol) and carbon tetrabromide (2.6 g, 7.9 nmol) in methylene chloride (10 ml) was cooled to 0° C. A solution of triphenyl phosphine (1.9 g, 7.3 nmol) in methylene chloride (10 ml) was added dropwise and the reaction was stirred for 5 min. Solvent evaporation and flash chromatography (silica gel, ethyl acetate-hexane, 5/95) gave 5-(2 bromoethyl)benzofurazan (1.2 g, 86%); 1H NMR (CDCl3) δ: 3.32 (t, 2H), 3.69 (t, 2H), 7.32 (d, 1H), 7.69 (s, 1H), 7.84 (d, 1H).

Provenance & Evidence