Discovery of C9H9IO2

According to the analysis of related databases, 1829-28-3, the application of this compound in the production field has become more and more popular.

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., Quality Control of Ethyl 2-iodobenzoate

To a 2-dram vial with a PTFE-lined cap was charged with acetal 1o (30.1 mg, 0.0980 mmol), ethyl 2-iodobenzoate (111 mg, 0.402 mmol), NBE-CO2Me (23.1 mg, 0.152 mmol), Pd(TFA)2 (3.3 mg, 0.00994 mmol), TFA-Gly-OH (3.3 mg, 0.0193 mmol), AgOAc (66.0 mg, 0.395 mmol), and DCE (2.00 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 preparative TLC (2:1 hexanes/EtOAc eluent) to afford arylation product 3opmono (13.6 mg, 30percent yield, Rf=0.21 in 2:1 hexanes/EtOAc) as a yellow oil and arylation product 3opdi together with an unidentified impurity (6.0 mg total). (20percent recovery of starting material 1o was also observed in the crude NMR prior to purification.) The impure arylation product 3opdi was then dissolved in MeOH (2.00 mL), HCl (gas) was bubbled through the mixture until the pH 1, and the mixture was stirred at room temperature for 23 h. Saturated aq. Na2CO3 (5 mL) and water (10 mL) were then added, and the mixture was extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine (15 mL) and dried over anhydrous Na2SO4. The solvent was concentrated by rotary evaporation, and the resulting residue was purified by preparative TLC (2:1 hexanes/EtOAc eluent) to afford biaryl alcohol 6opdi (3.3 mg, 8percent yield, Rf=0.21 in 2:1 hexanes/EtOAc) as a colorless oil. Monoarylation product (3opmono): 1H NMR: (400 MHz, CDCl3) delta 8.17 (d, J=8.5 Hz, 1H), 8.05 (s, 1H), 7.86 (d, J=7.2 Hz, 1H), 7.83 (d, J=8.2 Hz, 1H), 7.72 (app. t, J=7.7 Hz, 1H), 7.61-7.48 (m, 2H), 7.46-7.30 (m, 4H), 6.86 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 5.40 (d, J=13.2 Hz, 1H), 5.23 (d, J=13.2 Hz, 1H), 4.93 (d, J=11.1 Hz, 1H), 4.85 (d, J=11.1 Hz, 1H), 4.07 (q, J=7.2 Hz, 2H), 3.69 (s, 3H), 1.02 (t, J=7.2 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 168.5, 159.7, 156.1, 148.6, 138.7, 132.1, 131.63, 131.56, 130.83, 130.80, 130.6, 129.93, 129.85, 129.64, 129.56, 129.2, 129.1, 128.1, 128.0, 127.3, 127.2, 110.2, 103.4, 70.2, 70.1, 60.8, 55.5, 14.0. IR: (film) 1721, 1503, 1289, 1251, 1020 cm?1. HRMS: (ESI+) m/z calc’d for (M+H)+ [C28H25NO5+H]+: 456.1805, found 456.1813. Diarylation product alcohol (6opdi): 1H NMR: (400 MHz, CDCl3) delta 7.90 (d, J=7.8 Hz, 2H), 7.57-7.49 (m, 2H), 7.46-7.38 (m, 4H), 7.22 (s, 2H), 4.69 (d, J=5.9 Hz, 2H), 4.17 (app. br. s, 4H), 3.01 (s, 3H), 1.66 (t, J=5.9 Hz, 1H), 1.12 (t, J=7.0 Hz, 6H). 13C NMR: (125 MHz, CDCl3) delta 168.2, 153.7, 139.0, 136.0, 135.2, 131.6, 131.3, 129.9, 128.6, 127.5, 65.2, 61.0, 60.1, 14.1. IR: (film) 3473, 1717, 1291, 1254, 1131 cm?1.HRMS: (ESI+) m/z calc’d for (M+Na)+ [C26H26O6+Na]+: 457.1622, found 457.1627.

According to the analysis of related databases, 1829-28-3, the application of this compound in the production field has become more and more popular.

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