Benzoyl Peroxide → 4'-(Bromomethyl)-2-cyanobiphenyl

Participants

Reaction Steps

A solution of 5.59 g of 4′-methyl-2-cyanobiphenyl, 29 immol of N-bromosuccinimide, 9 mmol of benzoylperoxide and 500 mL of carbontetrachloride was refluxed for 3 hours. After cooling to room temperature, the resulting suspension was filtered and then concentrated in vacuo to provide the crude 4′-bromornethyl-2-cyanobiphenyl. The product was recrystallized from ether to yield 4.7 g of product; mp. 114.5°-120.0°. NMR (200 MHz, CDCl3)δ 7.82-7.37 (m, 8H); 4.50 (s, 2H). Anal. Calcd. for C14H10BrN: C, 61.79, H, 3.70; N, 5.15. Found: C, 62.15; H, 3.45; N, 4.98.

Provenance & Evidence