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【结 构 式】 
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【分子编号】34108 【品名】diethyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)-2-methylmalonate 【CA登记号】 |
【 分 子 式 】C20H21FO4 【 分 子 量 】344.3827432 【元素组成】C 69.75% H 6.15% F 5.52% O 18.58% |
合成路线1
该中间体在本合成路线中的序号：(II)By reaction of ethyl 2-fluoro-4-biphenylylacetate (I) first with diethyl carbonate and sodium ethoxide, and then with dimethyl sulfate in ethanol to give diethyl 2-fluoro-4-biphenylyl-alpha-methylmalonate (II), which was hydrolyzed with NaOH in ethanol and finally decarboxylated at 180-200 C. The starting product (I) was obtained as follows: the Ullman condensation of 4-bromo-3-nitroacetophenone (III) gives 2-nitro-4-acetylbiphenyl (IV), which was reduced to the corresponding amino compound (V). This, by the Schieman reaction was converted into 2-fluoro-4-acetylbiphenyl (VI), which by heating with sulfur and morpholine (B) gave 2-fluoro-4-biphenylylacetic acid (VII), and finally (VII) was esterified by refluxing with ethanol and H2SO4.
| 【1】 Adams, S.S.; et al.; 2-(Mono- and difluoro-4-biphenyl)propionic acids. US 3755427 . |
| 【2】 Thorpe, P.; Castaner, J.; Flurbiprofen. Drugs Fut 1976, 1, 7, 323. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (A) | 13364 | Benzene | 71-43-2 | C6H6 | 详情 | 详情 |
| (I) | 34107 | ethyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)acetate | C16H15FO2 | 详情 | 详情 | |
| (II) | 34108 | diethyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)-2-methylmalonate | C20H21FO4 | 详情 | 详情 | |
| (III) | 34109 | 1-(4-bromo-3-nitrophenyl)-1-ethanone | 18640-58-9 | C8H6BrNO3 | 详情 | 详情 |
| (IV) | 34110 | 1-(2-nitro[1,1'-biphenyl]-4-yl)-1-ethanone | C14H11NO3 | 详情 | 详情 | |
| (V) | 34111 | 1-(2-amino[1,1'-biphenyl]-4-yl)-1-ethanone | C14H13NO | 详情 | 详情 | |
| (VI) | 34112 | 1-(2-fluoro[1,1'-biphenyl]-4-yl)-1-ethanone | C14H11FO | 详情 | 详情 | |
| (VII) | 34113 | 2-(2-fluoro[1,1'-biphenyl]-4-yl)acetic acid | C14H11FO2 | 详情 | 详情 |