Azobisisobutyronitrile → 4-(Bromomethyl)naphthalene-1-carbonitrile

To a stirred solution of 4-methyl-1-naphthonitrile (5 g, 30 mmol) in CCl4 (50 mL) under argon atmosphere was added NBS (6.06 g, 34.09 mmol), and the reaction mixture was degassed for 30 min. AIBN (0.3 g, 2.1 mmol) was added, and the resultant reaction mixture was heated at reflux for 4 h. The reaction mixture was cooled to ambient temperature, diluted with water and extracted with CH2Cl2 (3×100 mL). The combined CH2Cl2 layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in n-Hexane) to afford the title compound as a white solid (3.8 g, 52%): mp 131-133° C.; 1H NMR (400 MHz, CDCl3) δ 8.33 (m, 1H), 8.24 (m, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.78 (m, 2H), 7.62 (d, J=8.0 Hz, 1H), 4.95 (s, 2H); ESIMS m/z 245.92 ([M+H]+); IR (thin film) 2217 cm−1.

1. customthe reaction mixture was degassed for 30 min
2. customthe resultant reaction mixture
3. temperaturewas heated
4. temperatureat reflux for 4 h
5. extractionextracted with CH2Cl2 (3×100 mL)
6. washThe combined CH2Cl2 layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in n-Hexane)

ORD record

ord-855692a365624312aba0239471aa5545

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226500B2