Synthetic Route of 4028-63-1, A common heterocyclic compound, 4028-63-1, name is 2,4,6-Trimethyliodobenzene, molecular formula is C9H11I, 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.
tert-Butyllithium (9.0 mL of a 1.7 mol/l solution in n-pentane, 15.3 mmol)was added to iodomesitylene (10) (1.51 g, 6.14 mmol) in Et2O (20 mL) at ?78 °C under inertatmosphere. After 30 min, CuCN (273 mg, 3.07 mmol) was added and the suspension stirred at?60 °C for 2 h. The reaction mixture was then treated with nitrobenzene (0.94 mL, 9.12 mmol)and allowed to warm up to room temperature overnight. An aqueous solution of NH3 (12.5percentw/w, 80 mL) was slowly added and the resulting residue was extracted with MTBE (3 x 50 mL).The combined organic layers were washed with water (50 mL) and brine (50 mL), dried overMgSO4, filtered, and the solvent was removed in vacuum. The product 11 could be obtained aftercolumn chromatography (SiO2, n-hexane, Rf 0.43) as a colorless solid (542 mg, 2.27 mmol,74percent), mp 98 °C (ref.27 99?100 °C). 1H NMR (300 MHz, CDCl3): delta 6.94 (s, 4 H), 2.34 (s, 6 H),1.87 (s, 12 H) ppm. 13C{1H} NMR (75 MHz, CDCl3): delta 137.0 (2 C), 136.0 (2 C), 135.5 (4 C),128.2 (4 CH), 21.1 (2 CH3), 19.8 (4 CH3) ppm. IR (ATR): 2997 (w), 2938 (m), 2916 (m), 1470(m), 1436 (m), 1375 (m), 1004 (m), 852 (s), 595 (m) cm?1. MS (EI, 70 eV), m/z (percent): 238 (99)[M+], 223 (100), 208 (33), 193 (25). Anal. calcd. for C18H22 (238.37): C 90.70, H 9.30; found C90.73, H 9.34.
The synthetic route of 4028-63-1 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Behler, Florian; Wickleder, Mathias S.; Christoffers, Jens; ARKIVOC; vol. 2015; 2; (2014); p. 64 – 75;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com