Electric Literature of 19099-54-8, A common heterocyclic compound, 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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.
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 GL,] 2.0 mmol, bench grade solvent), 2-isopropyliodobenzene (246 mg, 1.0 mmol) and 2- isopropylbenzenethiol (90% purity, 202 muL, 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 [FIL,] 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 as eluent to afford colorless oil as the titled product (245 mg, 91% yield). Rf= 0.5 [(HEXANE).’H] NMR (CDC13,300 MHz) 8 7.30 (d, 2 H, [J =] 7.2 Hz), 7.18-7. 24 (m, 2 H), 7.03-7. 05 (m, [4] H), 3.50 (hept, 2 H, J = 6.9 Hz), 1.25 (s, 3 H), 1.23 (s, [3 H). 13C NMR (CDC13,] 75 MHz) 6 149.2, 134.2, 132.1, 127.6, 126.7, 125.9, 30.9, 23.8. IR (neat, [CM”)] 3058,2962, 2929,2867. MS [(EI)] [FILZ] (relative intensity) 270 (100), 211 (90). HRMS [(EI),] Cald. for [CIUSDH22S] 270.1442 ; Found 270.1445.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com