Carbon tetrabromide → HCID 15228264, compound

Participants

Reaction Steps

To a solution of triphenylphosphine (2.83 g, 0.011 mol) in 100 mL of acetonitrile was added a solution of 5-nitro-3-(2-hydroxyethyl)indole (2.00 g, 0.0097 mol) in 25 mL of acetonitrile, followed by a solution of CBr4 (3.60 g, 0.011 mol) in 25 mL of acetonitrile, at 0° C. under Ar. The mixture was stirred at room temperature for 18 h and then another 0.283 g (1.1 mmol) of triphenylphosphine and 0.360 g (1.1 mmol) of CBr4 were added. After 2.5 h the mixture was diluted with ethyl acetate, washed (H2O, brine), dried (Na2SO4) and evaporated and the residue was chromatographed (SiO2 /ethyl acetate-hexane, 1:4) to give the title compound (2.27 g, 87%) as a yellow solid: IR (neat) 3370, 1334 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.69 (s, 1H), 8.60 (d, J=2.1 Hz, 1H), 7.98 (dd, J=9.0, 2.2 Hz, 1H), 7.54-7.49 (m, 2H), 3.76 (t, J=7.2 Hz, 2H), 3.32 (t, J=7.2 Hz, 2H).

Provenance & Evidence