402-07-3,Some common heterocyclic compound, 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, molecular formula is C8H6BrF3O, 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.
Synthesis of (2-(Hydroxy(2-methoxy-4-(trifluoromethyl)phenyl)methyl)- 1 ‘-tosyl-l – 1 ,3 ‘- bipyrrol-2’-yl)(2-methoxy-4-(trifluoromethyl)phenyl)methanone (37). To a solution of l-bromo-2-methoxy-4-(trifiuoromethyl)benzene (720 mg, 2.88 mmol) in dry THF (5 mL) at -78 C under N2 was slowly added n-BuLi (1.15 mL, 2.5 M in n-pentane, 2.88 mmol). After being stirred for 30 min, a solution of 36 (550 mg, 1.06 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4C1 (15 mL) solution and extracted with EtO Ac (10 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtO Ac/petroleum) to give 37 (400 mg, 54% yield) as a light yellow solid. 1H NMR (400 MHz, CDCI3) delta 2.44 (s, 3H), 3.59 (br s, 3H), 3.84 (s, 3H), 5.77 (br s, 1H), 6.17-6.32 (m, 3H), 6.49 (br s, 1H), 6.70 (br s, 1H), 6.83 (d, J= 7.6 Hz, 1H), 7.13 (br s, 1H), 7.21 (br s, 1H), 7.35-7.37 (m, 4H), 7.42 (d, J= 2.8 Hz, 1H), 7.92 (d, J= 8.0 Hz, 2H) ppm; 13C NMR (CDC13, 100 MHz) delta 21.67, 55.75, 55.88, 67.96, 105.60, 105.64, 108.13, 108.03, 111.28, 116.78, 116.78, 116.78, 120.85, 120.85, 124.97, 126.20, 127.10, 127.30, 127.63, 127.63, 129.14, 129.14, 129.98, 129.98, 132.50, 132.56, 133.21, 133.45, 135.92, 145.38, 155.48, 157.01, 180.50 ppm; IR (KBr) 3444, 3137, 2923, 1668, 1562, 1447, 1361, 1180, 1014, 752, 668 cm”1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-methoxybenzotrifluoride, its application will become more common.
Reference:
Patent; CHONGQING ZEIN PHARMACEUTICAL CO., LTD.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; QIN, Yong; CHENG, Chunwei; SONG, Hao; LI, Rongshi; LIU, Yan; WO2014/116634; (2014); A1;,
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