Potassium Iodide → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

Participants

Reaction Steps

A solution of 4-methyl-2'-nitro-1,1'-biphenyl (Step A) (6.0 g, 28.2 mmol), N-bromosuccinimide (4.99 g, 28.2 mmol). and AIBN (653 mg) in 75 mL of carbon tetrachloride was heated at reflux until a negative potassium iodide test was obtained (1.5 h). The reaction mixture was cooled and filtered. The filtrate was evaporated under vacuum to yield 8.41 g of crude product. 1H NMR revealed the product composition was approximatly 75% monobromo and 10% dibromo, in addition to 15% of unreacted starting material. 1H NMR. (200 MHz, CDCl3): δ4.53 (s, 2H), 7.2-7.7 (m, 7H), 7.85 (m, 1H). EI-MS: calculated for C14H10BrN 272; found 272,274 (M+).

Provenance & Evidence