Some common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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. 38573-88-5
EXAMPLE 200 Step-1: n-Butyl lithium (0.895 g, 0.0140 mol, 1.6 M in hexane) was added dropwise to a stirred solution of 2, 3-difluorobromobenzene (3.0 g, 0.0155 mol) in THF (40 ml) over a period of 20 min at -78 0C, and reaction was continued stirring for 2 h at the same temperature. Then, 4,6-dichloropyrimidine (2.316 g, 0.0155 mol) in THF (20 ml) was added drop wise to the generated 2,3-difluorophenyl lithium mixture over a period of 15 min at -78 ¡ãC, and reaction was continued stirring for 30 min. Then, the reaction mixture was slowly warmed to 0 ¡ãC and was quenched with water (30 ml), and then DDQ (3.53 g, 0.0155 mol) in THF (30 ml) was added portionwise with stirred for 10 min. The resultant reaction mixture was extracted with CH2Cl2 (3×50 ml), washed with brine (50 ml), dried (Na2SO4), and concentrated. The concentrated product was purified through silica column chromatography using pet. ether to afford step-1 product (1.1g, 27.1 percent) as an off white solid. Rf: 0.3 (100percent PE). 1H NMR (400 MHz, CD3OD): delta 8.82 (s, IH), 7.91-7.78 (m, IH), 7.48-7.45 (m, IH), 7.32-7.26 (m, IH). m/e (M+l): 260.8
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38573-88-5, its application will become more common.
Reference:
Patent; MIIKANA THERAPEUTICS, INC.; WO2008/154026; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary