364-11-4, A common compound: 364-11-4, name is 1-Bromo-4-iodo-2-(trifluoromethyl)benzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
To a solution of 1-bromo-4-iodo-2-(trifluoromethyl)benzene (246 mg, 0.701 mmol) in 1.4 mL of Et2O (C=0.5M) was added dropwise a 1.6M solution of BuLi in hexane (460muIota., 1.05 eq) at -78C. After 15 min of stirring, benzaldehyde (86muIota., 1.2 eq) was slowly added. The mixture was stirred for 4h at -75 C and then, hydrolyzed with water and with a 1M HC1 solution to acidify. The layers were separated. The aqueous layer was extracted with DCM (3>< 10mL). The combined organics were washed with brine, dried over MgSO4, filtered and solvents were removed in vacuo. The crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 93:7 to 90: 10) to afford the desired product in 76% yield (176 mg) as an uncoloured oil. 1H NMR (300 MHz, CDC13) delta 7.76 (d, J = 2.2 Hz, 1H), 7.65 (d, J = 8.3 Hz, 1H), 7.41 - 7.27 (m, 6H), 5.81 (s, 1H), 2.36 (s, OH); 13C NMR (75 MHz, CDCI3) delta 143.5 (C), 142.8 (C), 135.1 (d, J = 2.0 Hz, CH), 131.0 (CH), 130.2 (q, J = 31.3 Hz, C), 129.0 (CH), 128.5 (CH), 126.7 (CH), 125.9 (q, J = 5.4 Hz, CH), 123.0 (q, J = 273.6 Hz, C), 1 18.9 (q, J = 2.0 Hz, C), 75.4 (CH); MS (ESI) m/z : 313.0, 315.0 [M-OH, 79Br, 81Br]+; 348.0, 350.0 [M+NH4, 79Br, 81Br]+; 680.0 [2M+NH4, 79Br, 81Br]+.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-4-iodo-2-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; UNIVERSITA’ DEGLI STUDI DI MILANO – BICOCCA; UNIVERSITE DE GENEVE; UNIVERSITE CLAUDE BERNARD – LYON 1; GAMBACORTI-PASSERINI, Carlo; MOLOGNI, Luca; SCAPOZZA, Leonardo; BISSON, William; AHMED, Shaheen; GOEKJIAN, Peter; TARDY, Sebastien; ORSATO, Alexandre; GUEYRARD, David; BENOIT, Joseph; WO2013/167730; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com