Some common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, 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. Computed Properties of C11H14INO2
Step B [4-(t-Butoxycarbonylamino)phenyl]trimethylstannane The iodide (2.75 g; 8.62 mmol) from Step A of this Example, hexamethylditin (4.23 g; 12.91 mmol) and tetrakis(triphenylphosphine)palladium(0) were mixed together in anhydrous dioxane and subjected to a freeze-vac-thaw cycle to degas the solution and then the reaction heated to reflux under a nitrogen atmosphere for 6 h. The reaction mixture was then cooled to room temperature, poured into iced saturated brine and extracted with ether (3*250 ml). The ethereal layers were combined and washed with another portion of brine, dried over anhydrous magnesium sulfate powder and evaporated under reduced pressure to leave an orange mobile liquid. Chromatography of the liquid on silica gel using an eluant consisting of ether and hexanes in the ratio 1:19 v/v afforded 1.75 g (ca. 57%) of a material that was [4-(t-butoxycarbonylamino)phenyl]trimethylstannane that contained traces of the starting material. 1 H NMR (200 MHz, CDCl3): 0.23 (s, 9H) 1.47 (s, 9H) 6.45 (s, 1H) 7.25-7.40 (ABq, 4H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 159217-89-7, its application will become more common.
Reference:
Patent; Merck & Co., Inc.; US5726319; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com