Synthetic Route of 1829-28-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1829-28-3, name is Ethyl 2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.
To a 2-dram vial with a PTFE-lined cap was charged with acetal 1f (1.00 mL, 0.100 M in DCE, 0.100 mmol), ethyl 2-iodobenzoate (111 mg, 0.402 mmol), NBE-CO2Me (23.8 mg, 0.157 mmol), Pd(TFA)2 (3.4 mg, 0.0102 mmol), TFA-Gly-OH (3.4 mg, 0.0199 mmol), AgOAc (66.3 mg, 0.397 mmol), and DCE (1.00 mL). The resulting mixture was heated to 100° C. and stirred for 24 h. After cooling to room temperature, ethylenediamine (0.100 mL) was added, and the resulting mixture was stirred at 23° C. for 2 h. The mixture was filtered through a plug of silica gel, eluting with EtOAc (30 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (3:1 hexanes/EtOAc eluent) to afford arylation product 3fp (35.4 mg, 62percent yield, Rf=0.16 in 2:1 hexanes/EtOAc) as a colorless oil. 1H NMR: (500 MHz, CDCl3) delta 8.16 (d, J=8.5 Hz, 1H), 8.05 (s, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.75-7.68 (m, 1H), 7.59-7.54 (m, 1H), 7.49 (app. td, J=7.5, 1.2 Hz, 1H), 7.42-7.33 (m, 2H), 7.28 (s, 1H), 7.20 (s, 1H), 7.07 (s, 1H), 6.32 (s, 1H), 5.40 (d, J=13.2 Hz, 1H), 5.23 (d, J=13.2 Hz, 1H), 4.96 (d, J=11.6 Hz, 1H), 4.86 (d, J=11.6 Hz, 1H), 4.03 (q, J=7.1 Hz, 2H), 3.69 (q, J=7.1 Hz, 2H), 1.40 (s, 9H), 1.15 (t, J=7.1 Hz, 3H), 0.95 (t, J=7.1 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 168.9, 159.5, 154.6, 148.6, 142.5, 142.1, 141.8, 138.2, 131.5, 131.3, 130.8, 130.7, 129.92, 129.90, 129.7, 129.1, 128.07, 128.05, 127.5, 127.3, 126.3, 125.8, 125.5, 103.7, 80.2, 70.1, 70.0, 61.1, 45.2, 28.5, 14.1, 13.9. IR: (film) 1698, 1290, 1253, 1151, 758 cm?1.HRMS: (ESI+) m/z calc’d for (M+H)+ [C34H36N2O6+H]+: 569.2646, found 569.2651.
The chemical industry reduces the impact on the environment during synthesis Ethyl 2-iodobenzoate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; The University of Georgia Research Foundation, Inc; Ferreira, Eric; Li, Qiankun; (47 pag.)US2018/65909; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com