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90434-16-5

1-(BROMOMETHYL)-2-METHOXY-4-NITROBENZENE synthesis

3synthesis methods
-

Yield:90434-16-5 90%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 80; for 8 h;

Steps:

General synthesis procedure 11a

2-methoxy-1-methyl-4-nitrobenzene (500mg, 2.99mmol), NBS (586mg, 3.29mmol) and Benzoyl peroxide (72mg, 0.299mmol) were added into CCl4 (30mL) and stirred at 80°C for 8h. The reaction mixture was evaporated. The residue was chromatographed (silicagel, Hexane/EtOAc=100:1) to give 1-(bromomethyl)-2-methoxy-4-nitrobenzene (DC-TEADin11-1, 662mg, 90%) as a white solid. 1H NMR (400MHz, Chloroform-d) δ 7.82 (dd, J=8.3, 2.2Hz, 1H), 7.73 (d, J=2.2Hz, 1H), 7.49 (d, J=8.3Hz, 1H), 4.54 (s, 2H), 4.00 (s, 3H).

References:

Lu, Wenchao;Wang, Jun;Li, Yong;Tao, Hongru;Xiong, Huan;Lian, Fulin;Gao, Jing;Ma, Hongna;Lu, Tian;Zhang, Dan;Ye, Xiaoqing;Ding, Hong;Yue, Liyan;Zhang, Yuanyuan;Tang, Huanyu;Zhang, Naixia;Yang, Yaxi;Jiang, Hualiang;Chen, Kaixian;Zhou, Bing;Luo, Cheng [European Journal of Medicinal Chemistry,2019,vol. 184,art. no. 111767]