Application of 111771-08-5, A common heterocyclic compound, 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, molecular formula is C7H4FIO2, 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.
General procedure: Preparation of Intermediates 4 To a mixture of 2-iodine benzoic acids 1 (4 mmol), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (4.8 mmol)and N-hydroxybenzotrizole (0.48 mmol) were added amines(4.8 mmol) at room temperature. The reaction mixture wasstirred overnight and washed with water successively. Theorganic layer was dried over anhydrous sodium sulfate. Then,the solvent was removed under vacuum to afford crude com-pounds 2. 2-Iodine benzamides 2 (3.00 mmol) were added to30 mL triethylamine in a round-bottom flask, then the solutionwas degassed with nitrogen for 10 min. CuI (0.306 mmol) andPdCl2(PPh3)2 (0.1044 mmol) were added and the system wasplaced under nitrogen atmosphere. Trimethylsilylacetylene(6 mmol) was added dropwise over 3 min. And the mixture washeated with stirring at 608C overnight. The reaction was allowedto cool to room temperature and then filtered over Celite. Thefiltrate was concentrated and purified by column chromatogra-phy on silica gel with petroleum ether and ethyl acetate as sol-vents to give the intermediates 3. Then, compounds 3(1.73 mmol) were added to 15mL MeOH in a flask and mixedwith K2CO3 (1.73 mmol). The flask was placed under nitrogenatmosphere and the system was stirred for 15 min, after whichH2O was added to the flask. The organic layer was extractedwith ethyl acetate, dried over Na2SO4, and concentrated undervacuum. The crude oil was then purified by column chroma-tography on silica gel to get structures 4.
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:
Article; Li, Jiling; Zhang, Zhicheng; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong; Australian Journal of Chemistry; vol. 68; 10; (2015); p. 1543 – 1549;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com