38573-88-5,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.
4-(19): 1-(2,3-Difluorophenyl)-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone Isopropylmagnesiumchloride-LiCl complex (1.30 M in THF, 155.0 mL, 0.0715 mol) under nitrogen was cooled to 0-5¡ã C., and 2,3-difluorobromobenzene (13.8 g, 0.0715 mol, 1.50 equiv.) was added while T<10¡ã C. After 1 h at 0-5¡ã C., a solution of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (21.8 g, 0.048 mol, 1.0 equiv.) in THF (2.0 vols) was added while T<10¡ã C. The reaction mixture was stirred for 2.5 h and monitored for consumption of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (target>97percent). The reaction mixture was quenched by charging into cold sat. aq. NH4Cl (110 mL) and water (33 mL) while T<20¡ã C. 2-Methoxy-2-methylpropane (218 mL) was added and the layers were separated. The organics were washed with sat. aq. NH4Cl (65 mL) and 18percent aq. NaCl (44 mL). The organics were concentrated under vacuum T<25¡ã C. to a light yellow oil (21.6 g). 1H NMR (500 MHz, CDCl3) delta ppm 7.70-7.64 (m, 1H), 7.47-7.42 (m, 6H), 7.37-7.30 (m, 1H), 7.30-7.25 (m, 6H), 7.24-7.19 (m, 3H), 7.19-7.13 (m, 1H), 5.84-5.71 (m, 1H), 5.30 (d, J=17.3 Hz, 1H), 5.25 (d, J=10.4 Hz, 1H), 4.78 (dd, J=17.7, 3.1 Hz, 1H), 4.70 (dd, J=17.7, 3.1 Hz, 1H), 4.03 (dd, J=11.8, 6.5 Hz, 1H), 3.35 (dd, 1=9.8, 6.4 Hz, 1H), 3.18 (dd, J=9.8, 4.6 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta ppm 194.15 (dd, JCF=4.9, 2.4 Hz), 150.77 (dd, JCF=250.3, 14.1 Hz), 150.29 (dd, JCF=256.4, 13.9 Hz), 143.98, 135.34, 128.75, 127.76, 126.95, 125.70 (d, JCF=12.0 Hz), 125.16 (d, JCF=3.5 Hz), 124.55 (dd, JCF=6.4, 4.2 Hz), 121.62 (d, JCF=17.6 Hz), 118.83, 86.78, 81.35, 74.98 (d, JCF=9.5 Hz), 66.71.
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; EISAI R&D MANAGEMENT CO., LTD.; Takaishi, Mamoru; Ishida, Tasuku; US2014/179690; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary