4-(4-bromobutoxy)benzonitrile synthesis

Yield:34334-24-2 78%

Reaction Conditions:

with potassium hydroxide in dimethyl sulfoxide at 20; for 12 h;

Steps:

4.1.1 The preparation of 4-(3-bromopropoxy)benzonitrile (4a) and 4-(4-bromobutoxy)benzonitrile (4b)

General procedure: In a 250mL round bottom flask containing DMSO (100mL), powdered KOH (200mmol, 11.2g) was added. After stirring for 10min, 4-hydroxybenzonitrile (50mmol, 5.9g) was added followed immediately by 1,n-dibromo alkanes [n=3,4] (250mmol, n=3: 25.3mL, n=4: 29.8mL) and stirring was continued for 12h at room temperature. After this time. The mixture was poured into the water (1000mL) and extracted with dichloromethane (3×200mL), the combined organic extract were washed with water (5×100mL) and dried under Na₂SO₄ and the solvent was evaporated. The crudes were purified by column chromatography on silica gel eluting with a proper solvent (n-hexane until the separation of excess 1,n-dibromo alkanes and then a mixture of n-hexane/EtOAc 4:1) and the products were obtained in 78% yields.

References:

Shekouhy, Mohsen;Karimian, Somaye;Moaddeli, Ali;Faghih, Zeinab;Delshad, Yousef;Khalafi-Nezhad, Ali [Bioorganic and Medicinal Chemistry,2020,vol. 28,# 12,art. no. 115540]