Some common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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. Safety of 1-Iodo-3-(trifluoromethyl)benzene
The mixture of Intermediate-51a (150mg, 0.45mmol), l-iodo-3(trifluoromethyl)benzene (0.18g,0.68 mmol) and CS2CO3 (0.22 g, 0.68 mmol) in toluene (7mL) was degassed for 15 min by purging nitrogen followed by addition of bis (tri-tert-butylphosphine palladium(O) (11.53mg, 0.023 mmol) and tris dibenzylidene acetone dipalladium (0)(20.66mg,0.023 mmol). The reaction mixture was heated to 110C and further maintained for 20 hr at the same temperature. The reaction mixture was cooled to room temperature and progress of reaction monitored by TLC. The mixture was diluted with ethyl acetate, filtered through celite and concentrated under vacuum to give crude compound. This crude compound was further purified by flash chromatography using a mixture of 20% ethylacetate in hexane (0.17g, 79%).Ethereal HCl (2 mL) was added and stirred for 10 min. The solvent was evaporated and solid washed by diethyl ether (2 mL) followed by «-pentane (2 ml), dried to get HCl salt of title compound.m/z 477.2; *H NMR (400 MHz, DMSO-d6): delta 9.64 (bs, IH), 9.10 (bs, IH), 8.24 (d, 7=8.4 Hz, IH), 8.03 (t, 7=8.8 Hz, 2H), 7.89 (d, 7=7.2 Hz, IH), 7.63-7.48 (m, 6H), 7.37(d, 7=7.6 Hz, IH), 6.93 (d, 7=7.2 Hz, IH), 6.80-6.77 (m, 3H), 5.34 (m, lH), 4.28 (m, 1H),3.85 (m, lH), 3.47-3.10 (m, 3H), 2.03 (m, 2H), 1.67 (d, 7=6.8 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 401-81-0, its application will become more common.
Reference:
Patent; LUPIN LIMITED; SHUKLA, Manojkumar, Ramprasad; ANKUSH, Sarde, Gangaram; VIPUL, Pachpute, Dilip; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/127385; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com