Related Products of 77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Methyl 2-amino-5-(phenethylthio)benzoate (2) Synthesized using reported procedure with modification (see, e.g., Itoh, T; Mase, T. Org. Lett. 2004, 6, 4587-4590). To a round-bottom-flask under nitrogen were added methyl 2- amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), z-P^Net (775 mg, 1.05 mL, 6 mmol, 2.0 equiv.) and dry 1,4-dioxane (30 mL). Catalyst Pd2(dba)3 (137 mg, 0.15 mmol, 0.05 equiv.), Xantphos (173 mg, 0.3 mmol, 0.1 equiv.) were then added and the mixture were stirred for 15 minutes. 2-Phenylethanethiol (415 mg, 0.4 mL, 3 mmol, 1.0 equiv.) was added and then the mixture was heated to reflux for 16 hours. The reaction mixture was then allowed to cool down to room temperature. The reaction mixture was then filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=15:85) on silica gel to afford 2 (862 mg, 82%) as yellow oil which solidified upon standing. XH NMR (300 MHz, CDC13) delta 7.99 (s, 1H), 7.37-7.14 (m, 6H), 6.62 (d, J= 6.0 Hz, 1H), 5.80 (s, 2H), 3.87 (s, 3H), 3.04-2.99 (m, 2H), 2.87-2.82 (m, 2H); 1 C NMR (75 MHz, CDC13) delta 168.01, 149.86, 140.36, 138.81, 135.95, 128.50, 128.41, 126.28, 120.81, 117.42, 111.11, 51.64, 37.81, 35.94.
The synthetic route of 77317-55-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com