Adding a certain compound to certain chemical reactions, such as: 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 105202-02-6, name: 2-Iodo-5-(trifluoromethyl)aniline
To a solution of compound 53 (620 mg, 2.16 mmol) in DMF (5 mL) was added phenylacetylene (331 mg, 356 muL, 3.24 mmol), PdCI2(PPh3)2 (76 mg, 0.108 mmol), Cul (25 mg, 0.131 mmol) and Et3N (656 mg, 903 muL, 6.48 mmol) at 23 C. The reaction mixture was stirred for 6 h at 23 C before it was quenched with a saturated solution of NH4CI (10 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H20 (3 x 10 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes:EtOAc 5: 1 ) to give compound 54 (518 mg, 92%) as pale yellow solid. (0472) [00362] 1 H NMR (400 MHz, CDCI3) delta = 7.56 (m, 2H), 7.47 (dd, J = 8.5, 0.8 Hz, 1 H), 7.42 – 7.38 (m, 3H), 6.98 – 6.96 (m, 2H), 4.48 (brs, 2H); 13C NMR (101 MHz, CDCI3) delta = 147.8, 132.5, 131 .6, 131 .5 (q, J = 32.2 Hz), 128.7, 128.5, 124.0 (q, J = 272.3 Hz), 122.6, 1 14.3 (q, J = 3.8 Hz), 1 1 1 .2, 1 10.7 (q, J = 4.0 Hz), 96.5, 84.6; 19F NMR (376 MHz, CDCI3) delta = -63.13. m/z (ESI) 262.1 [M+H+].
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Reference:
Patent; THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO; GREIG, Iain; ZANDA, Matteo; TSENG, Chih-Chung; ROSS, Ruth; (134 pag.)WO2016/29310; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com