Carbon tetrabromide → 3-(2-bromoethyl)-5-fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-fluoro-3-(2-hydroxyethyl)indole (10.3 g, 0.056 mole) and CBr4 (24.8 g, 0.073 mole) in 100 mL of dry acetonitrile at 0° C. under Ar was added a solution of triphenylphosphine (19.6 g, 0.073 mole) in 200 mL of dry acetonitrile. The mixture was stirred at 0° C. for 1 h and then at room temperature for 2 h. The resulting mixture was evaporated and the residue was chromatographed (SiO2 /ethyl acetate-hexane=1:4) to give the product (8.50 g, 61%) as a brown solid; IR (neat) 3440 cm-1 ; 1Hnmr (80 MHz, CDCl3) δ: 7.75 (br s, 1H), 7.15-6.57 (m, 4H), 3.53-3.32 (m, 2H), 3.17-2.94 (m, 2H).

Provenance & Evidence