Sodium Cyanide → 2-Bromobenzyl cyanide

Participants

Reaction Conditions

Reaction Steps

N-Boc-protected 3-[2-(aminoethyl)phenyl]-2-propenoic acid (Compound 23) was prepared as outlined in Scheme IV. A mixture of o-bromobenzyl bromide (10.45 g; 41.81 mmol) and sodium cyanide (2.55 g; 52.25 mmol) in 100 ml of DMSO was heated at 60° C. for 5 hours. After being cooled, the reaction mixture was diluted with 200 ml of water and 200 ml of ethyl acetate. The layers were separated and the aqeous layer was extracted with any additional 100 ml of ethyl acetate. The combined organic layers were dried and concentrated, and the residue was purified on a flash column, eluting with 10% ether/hexane to obtain 6.63 g (81%) of 2-bromobenzyl cyanide 19, 1H NMR (CDCl3): δ3.83 (s, 2H); 7.18 (m,1h); 7.29 (t, 1H); 7.52 (d, 1H); 7.60 (d, 1H).

Provenance & Evidence