Electric Literature of 689291-89-2, A common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, molecular formula is C7H4BrIO, 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.
Compound 12 (32.0 mg, 0.103 mmol), 46 (55.6 mg, 0.103 mmol), PdCl2(PPh3)2 (3.6 mg, 0.0051 mmol), and CuI (1.96 mg, 0.0103 mmol) were added to Et3N (8 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt under N2 protection for 8 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 53, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 7:3) to yield compound 53 (21 mg, 0.029 mmol, 28%) as a white solid. Mp 75-76 C; IR (KBr) 2920, 2872, 2852, 2203, 1692, 1600, 1581, 1568, 1514, 1499, 1466, 1418 cm-1; 1H NMR (CDCl3, 500 MHz) delta 10.68 (s, 1H), 8.08 (d, J=1.5 Hz, 1H), 7.70 (dd, J=8.5, 1.5 Hz, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H), 7.02 (s, 1H), 7.01 (s, 1H), 6.90 (d, J=8.5 Hz, 1H), 4.06-4.02 (m, 4H), 3.85 (s, 3H), 1.90-1.84 (m, 4H), 1.59-1.47 (m, 4H), 1.42-1.27 (m, 24H), 0.90-0.87 (m, 6H); 13C NMR (CDCl3, 125 MHz) delta 191.3, 160.2, 154.7, 153.8, 137.4, 137.0, 134.5, 133.5, 130.5, 126.4, 123.3, 117.1, 116.5, 116.3, 115.8, 114.4, 112.1, 96.2, 95.0, 89.7, 85.0, 70.2, 69.7, 55.7, 32.3, 30.1, 30.05, 30.01, 30.0, 29.9, 29.8, 29.76, 29.70, 26.5, 23.1, 14.5; HRMS (CI) m/z calcd for C44H55BrO4 726.3284, found 727.3430 [M+H]+.
The synthetic route of 689291-89-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com