2-Iodothiophene

2-Iodothiophene (TP-I, Thiopheyl iodide, 2-ThioPhenyl iodide) is used as an intermediate in the synthesis of TP2P (ThioPhenyl-2-Propanone, 2-Thienylacetone). 2-Iodothiophene can react with ethyl acetoacetate and sodium ethoxide using CuI (Copper Iodide) and then reacted with hydrochloric acid and heated. 2-Iodothiophene can also undergo grignard reactions to obtain TP2Pol (ThioPhenyl-2-Propanonl, 2-Thienylisopropanol). 2-Iodothiophene has been obtained by addition of half of 50% aqueous nitric acid dropwise to a mixture of iodine and thiophene with vigorous stirring. As soon as the evolution of gases subsided the rest of the aqueous nitric acid was added to the reaction mixture and refluxed for 30 min. The organic layer was separated and steam distilled to obtain 2-iodothiophene. Iodination of thiophene with iodine and mercuric oxide at 0°C gave a mixture of 2-iodothiophene (70%) and 2,5-diiodothiophene. 2-Iodothiophene has been exclusively obtained by nitrating thiophene with a mixture of iodine and nitric acid at 90°C. An easy approach for iodination of thiophene is the reaction of iodine with lithiated thiophene.