Yield:-

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 70; for 6 h;

Steps:

4.1.12 General procedure for the synthesis of intermediates 9a-9g. Methyl 4-(bromomethyl)benzoate (9a)
General procedure: Compound 8a (4.505g, 30.00mmol), NBS (5.339g, 30.00mmol) and AIBN (492.6mg, 3.00mmol) were dissolved in CCl₄ (60mL). Then the mixture was stirred at 70°C. After completion, the mixture was concentrated under vacuum and purified by flash chromatography with ethyl acetate and petroleum ether (PE:EA=8:1) to give 4.582g of compound 9a in 67% yield as a white solid. ¹H NMR (500MHz, Chloroform-d) δ 8.02 (d, J=1.7Hz, 1H), 8.00 (d, J=2.0Hz, 1H), 7.46 (d, J=1.8Hz, 1H), 7.45 (d, J=1.9Hz, 1H), 4.50 (s, 2H), 3.92 (s, 3H). MS(ESI)m/e[M+H]⁺: 228.9. Synthesis of intermediates 9b-9g. The required compounds 8b-8g were reacted using a procedure similar to the synthesis of 9a to afford 9b-9g (58-72% yield).

References:

Gu, Yipei;Leng, Ying;Ning, Mengmeng;Shen, Jianhua;Tang, Xuehang;Yan, Hongyi;Ye, Yangliang [Bioorganic and Medicinal Chemistry,2021,vol. 43,art. no. 116280]