Synthesis
The general procedure for the synthesis of 6-bromoisoindolin-1-one from 5-bromo-2-bromomethylbenzoic acid methyl ester was as follows: gentle bubbling of ammonia into a 1:1 THF/MeOH mixture of 5-bromo-2-bromomethylbenzoic acid methyl ester (1 eq.) was carried out for 40 min at room temperature. Upon completion of the reaction, the reaction mixture was concentrated under vacuum. The concentrated residue was sonicated in CH2Cl2 for 15 min followed by filtration to afford the target product 6-bromo-2,3-dihydro-isoindol-1-one as a white solid (98% yield, 90% purity). Product mass spectral data: m/z (LC-MS, ESP): 212.3/214.3 [M + H]+, retention time R/T = 2.98 min.
References
[1] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 117
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183
[3] Patent: CN107474006, 2017, A. Location in patent: Paragraph 0050; 0051; 0054; 0056-0057; 0060; 0062-0063; 0066
[4] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 38
[5] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
