Azobisisobutyronitrile → 2-Amino-4-(bromomethyl)benzonitrile

2.2′-Azobisisobutyronitrile (AIBN) (1.31 g, 8 mmol) is added to a solution of N-bromosuccinimide (6.87 g, 38 mmol) and 2-benzylideneamino-4-methylbenzonitrile (7 g, 31.8 mmol) in carbon tetrachloride (250 mL), and the reaction mixture refluxed under nitrogen overnight. The reaction mixture is cooled and filtered through a plug of celite, and the celite washed with carbon tetrachloride (100 mL). The combined filtrate is washed with 1N HCl, saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The crude product is purified by column chromatography on silica with 10-20% ethyl acetate/hexanes. The combined product fractions are concentrated, and the resulting sticky solid is washed with ethyl ether/hexanes to give the product as a pale yellow solid (3.26 g, 15 mmol).

1. temperaturethe reaction mixture refluxed under nitrogen overnight
2. temperatureThe reaction mixture is cooled
3. filtrationfiltered through a plug of celite
4. washthe celite washed with carbon tetrachloride (100 mL)
5. washThe combined filtrate is washed with 1N HCl, saturated aqueous NaHCO3
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customThe crude product is purified by column chromatography on silica with 10-20% ethyl acetate/hexanes
9. concentrationThe combined product fractions are concentrated
10. washthe resulting sticky solid is washed with ethyl ether/hexanes

ORD record

ord-780e090598204e6ba7f8c13359e2c1a5

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06281227B1