Sodium Cyanide → 2-Bromobenzyl cyanide

Temperature

60 °C

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 aqueous 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): δ 3.83 (s, 2H); 7.18 (m, 1h); 7.29 (t, 1H); 7.52 (d, 1H);

1. temperatureAfter being cooled
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with any additional 100 ml of ethyl acetate
4. customThe combined organic layers were dried
5. concentrationconcentrated
6. customthe residue was purified on a flash column
7. washeluting with 10% ether/hexane

ORD record

ord-41181e9a1d114eacadc8e3966191fb15

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05444048