Reference of 17533-08-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17533-08-3 name is 1,2,4-Trifluoro-5-iodobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
To a stirred solution of 2,4,5-trifluoroiodobenzene (4) (1.50 g, 5.87 mmol), Pd(OAc)2 (26 mg, 2 mol %), triethylbenzylammonium chloride (1.32 g, 5.79 mmol), and NaHCO3 (0.98 g, 11.7 mmol) in 4 mL of DMF was added allyl alcohol (0.67 g, 0.79 mL, 11.6 mmol) under N2 atm. The resulting dark brown solution was heated at 45 C for 20 h. The reaction was quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (3¡Á25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by a silica gel column to give 5 (1.04 g; 95%). Light yellow liquid. (Rf: 0.2, 5:95 EtOAc/hexanes). GC/MS/MS (CI) (150 eV) m/z (rel intensity, %) 189.1 (M++1, 13), 144.9 (100). 1H NMR (400 MHz, CDCl3) delta=9.80 (br s, 1H, CHO), 7.04 (ddd, 1H, H-6′, JH,F=15.6, 8.4, 6.8 Hz), 6.88 (dt, 1H, H-3′, JH,F=10.0, 6.8 Hz), 2.92 (A2 part of A2X2 system, quasi t, 2H, 2¡ÁH-3, J=7.2 Hz), 2.78 (X2 part of A2X2 system, quasi t, 2H, 2¡ÁH-2, J=7.2 Hz). 13C NMR (100 MHz, CDCl3) delta=200.4 (C-1), 156.1 (ddd, C-2′, JC,F=242.7, 9.1, 2.6 Hz), 148.9 (ddd, C-4′, JC,F=248.4, 14.1, 12.4 Hz), 146.8 (ddd, C-5′, JC,F=243.4, 12.4, 3.7 Hz), 123.8 (ddd, C-1′, JC,F=18.1, 5.5, 4.3 Hz), 118.4 (dd, C-6′, JC,F=19.0, 5.7 Hz), 105.6 (dd, C-3′, JC,F=28.1, 20.6 Hz), 43.7 (C-2), 21.4 (C-3). IR (neat) 3065, 2934, 2829, 2725, 1725, 1632, 1522, 1425, 1388, 1333, 1211, 1152, 1099 cm-1.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2,4-Trifluoro-5-iodobenzene, and friends who are interested can also refer to it.
Reference:
Article; Fistikci, Meryem; Gundogdu, Ozlem; Aktas, Derya; Secen, Hasan; Sahin, M. Fethi; Altundas, Ramazan; Kara, Yunus; Tetrahedron; vol. 68; 12; (2012); p. 2607 – 2610;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com