1,2,4,5-四氟苯置于盐酸,正丁基锂,Dimethyl Sulfide Borane,三溴化磷,对甲苯磺酸,三氟乙酸体系中,用 四氢呋喃,甲苯 作为反应溶剂,化学反应 4.58H,反应生成 2,3,5,6-四氟对二溴苄
参考文献:Fluorinated Molecules Relevant To Conducting Polymer Research
标题:Fluorinated Molecules Relevant To Conducting Polymer Research
摘要:The Synthesis Of Versatile Fluorine Compounds For Conducting Polymer Research On Fluorinated Materials Is Presented. 1,2,4,5-Tetrafluorobenzene Was Converted To 1,2,4,5-Tetrafluorobenzaldehyde (1) And Protected As An Acetal. This Gave The Acetals 1,2,4,5-Tetrafluoro-3(1,3-Dioxol-2-yl)Benzene (2A) And 1,2,4,5-Tetrafluoro-3-(5,5-Dimethyl-1,3-Dioxan-2-yl)Benzene (2B). Compounds 2A And 2B Were Converted Into The Semiprotected 2,3,5,6-Tetrafluoroterephthaldehydes: 1,2,4,5-Tetrafluoro-3-(1,3-Dioxol-2-yl)-6-Formylbenzene (3A) And 1,2,4,5-Tetrafluoro-3-(5,5-Dimethyl-1,3-Dioxan-2-yl)-6-Formylbenzene (3B). While 3A Was Easily Deprotected To Give 2,3,5,6-Tetrafluoroterephthaidehyde (4) Compound 3B Proved Very Resilient To Hydrolysis And Gave A 1: 1 Mixture Of 4 And 1,2,4,5-Tetrafluoro-3,6-Bis(5,5-Dimethyl-1,3-Dioxan-2yl)Benzene (5). Compound 4 Was Reduced To 1,2,4,5-Tetrafluoro-3,6-Dihydroxymethylbenzene (6) And Converted Into 1,2,4,5-Tetrafluoro-3,6-Dibromomethylbenzene (7). Compound 7 Was Finally Converted Into 1,2,4,5-Tetrafluoro-3,6-Bis(Diethylphosponylmethyl)Benzene (8). Compounds 4 And 8 Are Versatile Fluorinated Molecules That Can Be Used To Replace Their Hydrogen Counterparts In Many Molecules And Materials. To Illustrate This Compounds 4 And 8 Were Oligomerised To Give Partially Fluorinated Polyphenylenevinylene (9). (C) 2002 Elsevier Science B.V. All Rights Reserved.
DOI:10.1016/s0022-1139(02)00289-0