4,5-dichloro-2-methylbenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution 4,5-Dichloro-2-methyl-benzonitrile 7 (6.3 g, 33.9 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (9.0 g, 50.8 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield the tittle compound 4.0 g. (45%). 1H NMR (400 MHz, CDCl3) δ7.75 (s, 1 H, Ar), 7.66 (s, 1 H, Ar), 2.55 (s, 2 H, CH3). The reaction mixture was refluxed 6 hrs filtered concentrated partitioned between ether and water The ether layer was dried concentrated purified by silica gel chromatography (10% ether/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution 4,5-Dichloro-2-methyl-benzonitrile 7 (6.3 g, 33.9 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (9.0 g, 50.8 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield the tittle compound 4.0 g. (45%). 1H NMR (400 MHz, CDCl3) δ7.75 (s, 1 H, Ar), 7.66 (s, 1 H, Ar), 2.55 (s, 2 H, CH3). The reaction mixture was refluxed 6 hrs filtered concentrated partitioned between ether and water The ether layer was dried concentrated purified by silica gel chromatography (10% ether/hexanes)