化学合成。
化学合成
合成路线 1（1. 合成：955959-84-9）
产率：93%
合成条件：With tetrakis(triphenylphosphine) palladium (0) ; potassium carbonate In tetrahydrofuran; water at 80℃; for 8 h; Inert atmosphere
实验步骤：在氮气氛下，将二苯并呋喃-4-基硼酸（100g，472mmol）溶于1,000mL四氢呋喃（THF）1-溴-4-碘苯（160g，556mmol）和四（三苯基膦）钯（5.45）中。 向其中加入g，4.72mmol）并搅拌。加入用水饱和的碳酸钾（78.3g，566mmol），并将混合物在80℃下加热回流8小时。 反应完成后，将水加入到反应混合物中，并将混合物用二氯甲烷（DCM）萃取。 然后，用无水MgSO 4除去水，过滤并减压浓缩。通过快速柱色谱法纯化由此获得的残余物，得到化合物I-9（142g，93％）。
参考文献：
- [1] Patent: KR2015/24669, 2015, A. Location in patent: Paragraph 0151-0153 [2] Patent: KR2016/8651, 2016, A. Location in patent: Paragraph 0155-0157 [3] Patent: KR2016/12846, 2016, A. Location in patent: Paragraph 0217; 0218; 0219 [4] Patent: KR2015/130221, 2015, A. Location in patent: Paragraph 0339-0341 [5] Patent: KR101531614, 2015, B1. Location in patent: Paragraph 0827-0830 [6] Patent: TW2016/2060, 2016, A. Location in patent: Paragraph 0091 [7] Patent: EP2163550, 2010, A1. Location in patent: Page/Page column 51-52 [8] Patent: EP2295421, 2011, A1. Location in patent: Page/Page column 49 [9] Patent: EP2738166, 2014, A1. Location in patent: Paragraph 0159-0160 [10] Patent: EP2762478, 2014, A1. Location in patent: Paragraph 0184; 0185 [11] Patent: EP2891648, 2015, A1. Location in patent: Paragraph 0106-0107 [12] Patent: EP2891653, 2015, A1. Location in patent: Paragraph 0105; 0106 [13] Patent: CN105431417, 2016, A. Location in patent: Paragraph 0202; 0203; 0204; 0205 [14] Patent: US9966541, 2018, B2. Location in patent: Page/Page column 101-102 [15] Patent: KR2018/44695, 2018, A. Location in patent: Paragraph 0201-0205 [16] Patent: WO2012/141499, 2012, A1. Location in patent: Page/Page column 18-19 [17] Patent: WO2004/99170, 2004, A2. Location in patent: Page 52-53 [18] Patent: WO2006/55625, 2006, A2. Location in patent: Page/Page column 89-90 [19] Patent: WO2006/55725, 2006, A2. Location in patent: Page/Page column 109-110; 126-127 [20] Patent: WO2004/99171, 2004, A2. Location in patent: Page 47-48; 65-66 [21] Patent: EP2177516, 2010, A1. Location in patent: Page/Page column 48 [22] Patent: EP2484665, 2012, A1. Location in patent: Page/Page column 65 [23] Patent: EP2502908, 2012, A1. Location in patent: Page/Page column 40 [24] Patent: US2012/273766, 2012, A1. Location in patent: Page/Page column 71 [25] Patent: KR2015/84657, 2015, A. Location in patent: Paragraph 1184 [26] Patent: KR101551591, 2015, B1. Location in patent: Paragraph 0316-0317 [27] Patent: KR101486562, 2015, B1. Location in patent: Paragraph 0834-0838 [28] Patent: US2018/97184, 2018, A1. Location in patent: Paragraph 0227; 0228; 0229 [29] Patent: KR2018/61825, 2018, A. Location in patent: Paragraph 0210-0213 [30] Patent: KR2018/60582, 2018, A. Location in patent: Paragraph 0196-0198 [31] Patent: KR2018/74172, 2018, A. Location in patent: Paragraph 0234-0237
合成路线 2（2. 合成：955959-84-9）
产率：13.7 g
合成条件：With tetrakis(triphenylphosphine) palladium (0) ; potassium carbonate In ethanol; water; toluene at 80℃; for 5 h;
实验步骤：在80℃，4-二苯并呋喃硼酸（13.3g），1,4-二溴苯（10g），四（三苯基膦）钯（3.02g），甲苯（158mL），乙醇（65mL），水（65mL）和钾 将碳酸盐（21.69g）搅拌5小时。 通过薄层色谱监测反应。 反应完成后，将其用水（100mL）淬灭并用乙酸乙酯（100mL）萃取。 用水（3×30mL）萃取有机层并用无水硫酸钠干燥。 通过硅藻土收集乙酸乙酯层，并通过柱色谱进一步纯化。 然后，在真空旋转蒸发下将乙酸乙酯层蒸发至干，得到13.7g 4-（4'-溴苯基）二苯并呋喃。
参考文献：
- [1] Patent: CN105585555, 2016, A. Location in patent: Paragraph 0097; 0098
合成路线 3
产率：94%
合成条件：With tetrakis(triphenylphosphine) palladium (0) ; potassium carbonate In methanol; toluene at 65℃; for 4 h; Inert atmosphere
实验步骤：一般步骤：6克1,3-二溴-5-碘苯，2.2克苯基硼酸，1.5克四（三苯基膦）钯（0），4.6克碳酸钾，60毫升甲苯和20毫升甲醇 在氮气氛下将其置于250ml圆底三颈烧瓶中并在65℃下搅拌4小时。将反应溶液冷却并用二氯甲烷和水萃取。 浓缩萃取液，然后使用二氯甲烷和正己烷的混合溶剂对浓缩溶液进行柱色谱，浓缩，得到6.08g 3,5-二溴联苯（产率：71％）。
参考文献：
