4-氰基-3-氟苄溴主要用于医药和农药领域,具体用途未在提供的信息中详细说明。
医药; 农药
合成路线 1(1. 合成:222978-03-2)
产率:88.79%
合成条件:With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 12 h; Reflux
实验步骤:3-氟-4-腈甲苯1(10g,74.07mmol)溶于氯仿200mL,加入BPO 1g,搅拌溶解,分批加入NBS(19.77g,11.11mmol),回流12h,冷却,反应溶液饱和 用碳酸氢钠水溶液洗涤3次,洗涤适量水3次,用饱和盐水洗涤3次,减压蒸发溶剂,柱色谱为淡黄色液体14.00g,收率88.79%。
参考文献:
- [1] Patent: CN106810552, 2017, A. Location in patent: Paragraph 0068; 0070; 0071 [2] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344 [3] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352 [4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930 [5] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 2107 - 2108 [6] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2483 - 2486 [7] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1411 - 1415 [8] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622 [9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4568 - 4574 [10] Patent: US6506738, 2003, B1 [11] Patent: WO2011/94890, 2011, A1. Location in patent: Page/Page column 118 [12] Patent: US2012/4198, 2012, A1. Location in patent: Page/Page column 32 [13] Patent: WO2014/144545, 2014, A2. Location in patent: Page/Page column 51
合成路线 2(3. 合成:222978-03-2)
产率:65%
合成条件:With N-Bromosuccinimide; sodium thiosulfate In tetrachloromethane; water
实验步骤:向2-氟-4-甲基 - 苄腈(1.45g,10.7mmol)的CCl 4(100mL)溶液中加入1,1'-偶氮二(环己烷甲腈)(0.240g,0.982mmol)和NBS(2.19g, 12.3毫摩尔)。 将混合物搅拌并加热回流过夜,然后冷却至室温。 加入Na 2 S 2 O 3(5g)的H 2 O(100mL)溶液,收集有机层。 水层用CH 2 Cl 2(3×50mL)萃取,合并萃取物,用Na 2 SO 4干燥。 过滤后,通过真空蒸发除去溶剂,并将残余物在硅胶柱上(1:10 EtOAc /己烷)纯化,得到4-溴甲基-2-氟 - 苄腈,为浅黄色油状物(1.49g,65%)。。 1H NMR(CDCl3)δ4.45(s,2H),7.24-7.30(m,2H),7.60(dd,1H,J = 6.3,8.1Hz)。
参考文献:
- [1] Patent: US2005/154201, 2005, A1