4-Bromo-3,5-dichlorobenzonitrile synthesis

Yield:1160574-40-2 87.7%

Reaction Conditions:

with n-Amyl nitrite;copper(ll) bromide in acetonitrile at 0 - 20;

Steps:

Step 1: Synthesis of 4-bromo-3,5-dichlorobenzonitrile (2-5)

The solution of amyl nitrite (468 mg, 4.0 mmol) in CH3CN (3 mL) was added slowly to a stirred solution of 4-amino-3,5-dichlorobenzonitrile (500 mg, 2.7 mmol) and cuprous bromide (723 mg, 3.24 mmol) in CH3CN (5 mL) at 0 °C, then the reaction mixture stirred at room temperature overnight, water (30 mL) was added , the mixture was extracted by ethyl acetate (30 mL×3), the organic layer was washed with brine and was dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to afford 4-bromo-3,5-dichlorobenzonitrile 587 mg (87.7% of yield).

References:

Sun, Nannan;Huang, Yafei;Yu, Mingcheng;Zhao, Yunpeng;Chen, Ji-An;Zhu, Chenyu;Song, Meiqi;Guo, Huimin;Xie, Qiong;Wang, Yonghui [European Journal of Medicinal Chemistry,2020,vol. 202,art. no. 112536] Location in patent:supporting information