Some common heterocyclic compound, 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, molecular formula is C7H6BrIO, 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. Formula: C7H6BrIO
To a solution of 4-bromo-1-iodo-2-methoxy-benzene (11.44 mmol, 3.581 g) in dryTHF (17.91 mL) under an atmosphere of nitrogen at -78C was added a solution ofisopropylmagnesium chloride in THF (1.3 mol/L, 11.0 mL, 14.30 mmol) over a period of 10 minutes, maintaining the reaction temperature between -65 and -70C. After stirring for 20 minutes, the reaction mixture was warmed to room temperature over one hour. The reaction mixture was cooled again to -78C and a solution of furan-2-carbaldehyde (13.73 mmol, 1.319 g) in THF (3.581 mL) was added over 5 minutes, whilst maintaining the reaction temperature between -65 and -70C. After 30 minutes, the reaction was allowed to warm to room temperature and stirred for a further 60 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate, thecombined organic phase was dried over magnesium sulfate and the solvent removed in vacuo. The resulting residue was purified by silica gel flash chromatography (gradient elution: 0-30% ethyl acetate in hexane) to produce (4-bromo-2-methoxy- phenyl)-(2-furyl)methanol as an orange oil (1.55g, 48%). 1H NMR (400MHz, CDCI3) 7.42-7.34 (m, 1H), 7.26 (s, 1H), 7.17-7.09 (m, 1H), 7.06-6.98 (m, 1H), 6.39-6.28(m, 1H), 6.13-6.06 (m, 1H), 6.04-5.89 (m, 1H), 3.82 (s, 3H), 2.91 -2.60 (m, 1H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 791642-68-7, its application will become more common.
Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HENNESSY, Alan, Joseph; HACHISU, Shuji; WILLETTS, Nigel, James; DALE, Suzanna, Jane; (70 pag.)WO2018/114584; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com