| 74.7% |
With NBS; azobisisobutyronitrile In Carbon tetrachloride Reflux; |
19A
4-methyl-1-naphthyl acetonitrile 2.50 g (14.95 mmol) dissolved in 40 mL of tetrachloro methane and, N- bromosuccinimide 3.19g (17.94 mmol) and 2,2'-azobis-2-methyl the propanenitrile 245 mg (1.50 mmol) was added. The mixture was stirred overnight at reflux temperature. After cooling, the product was filtered. 4- (bromomethyl) -1-naphthoyl nitrile to give the 2.75 g (74.7% of theory) 90% purity, which was reacted without further purification |
| 52% |
With NBS; azobisisobutyronitrile In Carbon tetrachloride for 4h; Reflux; Inert atmosphere; |
59
Example 59Preparation of 4-(bromomethyl)-1-naphthonitrile (CI66); 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 H2O 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. |
| 52% |
Stage #1: 4-methyl-1-naphthalenenitrile With NBS In Carbon tetrachloride for 0.5h; Inert atmosphere;
Stage #2: In Carbon tetrachloride for 4h; Reflux; Inert atmosphere; |
59 Example 59: Preparation of 4-(Bromomethyl)-l-naphthonitrile (CI66)
Example 59: Preparation of 4-(Bromomethyl)-l-naphthonitrile (CI66) To a stirred solution of 4-methyl-l-naphthonitrile (5 g, 30 mmol) in CC14 (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 H20 and extracted with CH2CI2 (3 x 100 mL). The combined CH2CI2 layer was washed with brine, dried over Na2S04, and concentrated under reduced pressure. The residue was purified by flash column chromatography (S1O2, 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; ]H NMR (400 MHz, CDCI3) δ 8.33 (m, 1H), 8.24 (m, 1H), 7.88 (d, / = 8.0 Hz, 1H), 7.78 (m, 2H), 7.62 (d, / = 8.0 Hz, 1H), 4.95 (s, 2H); ESIMS m/z 245.92 ([M+H]+); IR (thin film) 2217 cm"1. |
| 52% |
With NBS; azobisisobutyronitrile In Carbon tetrachloride for 4h; Inert atmosphere; Reflux; |
59 Example 59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66)
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 H2O 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. |
| 52% |
With NBS; azobisisobutyronitrile In Carbon tetrachloride for 4h; Inert atmosphere; Reflux; |
59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66)
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 H2O 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. |
| 52% |
Stage #1: 4-methyl-1-naphthalenenitrile With NBS In Carbon tetrachloride for 0.5h; Inert atmosphere;
Stage #2: With azobisisobutyronitrile In Carbon tetrachloride for 4h; Inert atmosphere; Reflux; |
59 Preparation of 4-(bromomethyl)-1-naphthonitrile (CI66)
To a stirred solution of 4-methyl-1-naphthonitrile (5 g, 30 mmol) in CC14 (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 H20 and extracted with CH2C12 (3 x 100 mL). The combined CH2C12 layer was washed with brine, dried over Na2S04, and concentrated under reduced pressure. The residue was purified by flash column chromatography (Si02, 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, CDCI3) δ 8.33 (m, 1H), 8.24 (m, 1H), 7.88 (d, / = 8.0 Hz, 1H), 7.78 (m, 2H), 7.62 (d, / = 8.0 Hz, 1H), 4.95 (s, 2H); ESIMS m/z 245.92 ([M+H]+); IR (thin film) 2217 cm-1. |
| 52% |
Stage #1: 4-methyl-1-naphthalenenitrile With NBS In Carbon tetrachloride for 0.5h; Inert atmosphere;
Stage #2: With azobisisobutyronitrile In Carbon tetrachloride for 4h; Reflux; |
59 Example 59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66)
Example 59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66) 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. |
|
With NBS; dibenzoyl peroxide In Carbon tetrachloride |
|
|
With NBS In Carbon tetrachloride for 4h; Heating; Irradiation; Yield given; |
|
|
With NBS; azobisisobutyronitrile In Carbon tetrachloride Reflux; |
42.A 4-Formyl-1-naphthonitrile
a): N-bromosuccinimide, 2,2'-azobis-2-methylpropanenitrile, tetrachloromethane, reflux; b): N-methylmorpholine N-oxide, acetonitrile, 3 Å molecular sieves; Example 42A 4-Formyl-1-naphthonitrile 2.50 g (14.95 mmol) of 4-methyl-1-naphthonitrile are dissolved in 40 ml of tetrachloromethane and 3.19 g (17.94 mmol) of N-bromosuccinimide and 245 mg (1.50 mmol) of 2,2'-azobis-2-methyl-propanenitrile are added. The mixture is stirred at the reflux temperature overnight. After cooling, the product is filtered off. 2.75 g (74.7% of theory) of 4-(bromomethyl)-1-naphthonitrile are obtained in a purity of 90% and are reacted without further purification. |
|
With NBS |
|
|
With NBS; azobisisobutyronitrile In Carbon tetrachloride; hexane; ethyl acetate |
59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66)
Example 59 Preparation of 4-(Bromomethyl)-1-naphthonitrile (CI66) 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. |
| 10.9 g |
With NBS; dibenzoyl peroxide In Carbon tetrachloride for 3h; Reflux; |
|
|
With NBS; dibenzoyl peroxide In Carbon tetrachloride for 3h; Reflux; |
A CCl4 (60 mL) solution of 1-cyano-4-methylnaphthalene(7.77 g, 46.5 mmol), N-bromosuccinimide (8.28 g, 46.5 mmol),benzoyl peroxide (cat) was refluxed for 3 h. Solid was removedbyfiltration, and solvent was removed in vacuo. The product,1-cyano-4-(bromomethyl)naphthalene (10.9 g, 44.5 mmol, 96% yield) was used without purification. Yellow solid; 1H NMR (CDCl3,300 MHz) δ4.93 (s, 2H), 7.59-8.33 (m, 6H) ppm. |
|
With NBS; azobisisobutyronitrile In 1,2-dichloro-ethane at 72℃; Inert atmosphere; |
28.28a
Under nitrogen protection, 4-methyl-1-naphthonitrile (400 mg, 2.4 mmol, 1.0 equivalent), N-bromosuccinimide (511 mg, 2.87 mmol, 1.2 equivalent) and azobisisobutyl A solution of nitrile (78.6 mg, 0.479 mmol, 0.2 equivalent) in dichloroethane (10 mL) was stirred at 72°C overnight. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to obtain the crude product 4-(bromomethyl)-1-naphthonitrile (678 mg, crude product). The product does not require further purification and is used directly in the next step. |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
