Synthesis
General procedure for the synthesis of methyl 2-aminobenzoate from bromobenzene and methyl o-aminobenzoate: 15 g of methyl o-aminobenzoate, 15.6 g of bromobenzene, 0.9 g of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.4 g of tri-tert-butylphosphine (P(t-Bu)3), and 28.6 g of tertiary butylsodium alcohol (Na(t-BuO)) were added, under nitrogen protection, to a round bottom flask followed by addition of 100 mL of toluene as solvent. The mixture was stirred and heated to reflux. Upon completion of the reaction, the reaction mixture was cooled to room temperature and washed with dichloromethane and water. The organic layer was separated, dried over anhydrous magnesium sulfate (MgSO4), filtered and purified by column chromatography to give the final methyl 2-(phenylamino)benzoate in a yield of 21.0 g in 93%.
References
[1] Tetrahedron, 2006, vol. 62, # 48, p. 11100 - 11105
[2] Patent: TWI579270, 2017, B. Location in patent: Paragraph 0094; 0095
[3] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646
[4] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8107 - 8109
[5] Patent: KR2016/102142, 2016, A. Location in patent: Paragraph 0215; 0218; 0219
