Application of 19099-54-8, These common heterocyclic compound, 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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.
Cu (I) iodide (38 mg, 0.2 mmol) and potassium carbonate (276 mg, 2.0 mmol) were charged into a screw-capped test tube with Teflon-lined septum. The tube was evacuated and backfilled with argon (3 cycles). [TERT-AMYL] alcohol (2-methyl-2-butanol) (1.0 [ML,] bench grade solvent without degassing and pre-drying), ethylene glycol (111 [. 1L,] 2.0 mmol, bench grade solvent), 2-isopropyliodobenzene (246 mg, 1.0 mmol) and 4- methoxythiolphenol (147 [AL,] 1.2 mmol) were added by syringes at room temperature. The tube was heated to [100 C] and stirred for 24 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 [FL,] GC standard) were added. The aliquot was analyzed GC. The reaction mixture was then filtered and concentrated. The crude product was purified by column chromatography on silica gel using [HEXANE/ETHYL] acetate = 40/1 as eluent to afford white solid as the titled product (241 mg, 94% yield). [RIF= 0.] 6 (hexane/ethyl acetate = 20/1). Melting point; 63-65 [C. LH] NMR [(CDC13,] 300 MHz) 8 7.32 (dt, 2 H, J= 2.1 Hz, 8.7 Hz), 7.25-7. 28 (m, 1 H), 7.19 (dt, 1 H, [J=] 2.1 Hz, 8.1 Hz), 7.03-7. 06 (m, 2 H), 6.88 (dt, 1 H, J= 2.4 Hz, 9.0 Hz), 3.82 (s, 3 H), 3.53 (hept, 1 H, J= 6.9 Hz), 1.27 (s, 3 H), 1.25 (s, 3 H). 13C NMR [(CDC13,] 75 MHz) [8 159.] 5,147. 8,135. 9,134. 5,130. 2,126. 9,126. 5,125. 7,125. 6,115. 2,55. 7,30. 7, 23.7. IR (neat, [CM”)] 3071,3068, 3011,2952, 2857. MS [(EI)] [M/Z] (relative intensity) 258 (100), 241 (20), 149 (30). Anal. Cald. for [C16HI80S,] Cald. C: 74.38, H: 7.02 ; Found C: 74.57, H: 7.04.
Statistics shows that 1-Iodo-2-isopropylbenzene is playing an increasingly important role. we look forward to future research findings about 19099-54-8.
Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com