Carbon tetrabromide → 3-(2-Bromoethyl)-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methyl-3-(2-hydroxyethyl)indole (4.00 g,0.023 mol) in 50 mL of acetonitrile at -20° C. under Ar was added a solution of CBr4 (10.16 g, 0.031 mol) in 25 mL of acetonitrile, followed by a solution of triphenylphosphine (8.00 g, 0.031 mol) in 125 mL of acetonitrile. The mixture was stirred and allowed to warm to 0° C. over 2 h. The resulting mixture was evaporated and the residue was chromatographed (SiO2 /hexane, then ethyl acetate-hexane=1:4) to give the product (4.00 g, 74%) as a brown oil: IR (neat) 2940, 1617, 1552 cm-1 ; 1Hnmr (200 MHz, CDCl3) δ 7.58 (d, J=7.6 Hz, 1H), 7.33-7.09 (m, 3H), 6.95 (s, 1H), 3.77 (s, 3H), 3.62 (t, J=7.9 Hz, 2 H), 3.32 (t, J=7.7 Hz, 2H).

Provenance & Evidence