Electric Literature of 14452-30-3, A common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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.
To a cooled (-40 C) stirred solution of TiCH (11 mL of a 1.0 M sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5.5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min iodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an additional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnesium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil. 1-tert-Butyl-3-iodo-benzene. To a cooled (-40 C) stirred solution of TiCH (11 mL of a 1.0 M sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5. 5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min lodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an addtional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnesium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil ; 1H NMR (300 MHz, CDCI3) 5 7.71 (t, J = 2.0 Hz, 1 H), 7.51 (dt, J = 7.7, 1.3 Hz, 1 H), 7.35 (app d, J = 7.7 Hz, 1 H), 7.03 (t, J= 7. 9 Hz, 1 H), 1.29 (s, 9H).
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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com