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【结 构 式】 
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【分子编号】27338 【品名】2-[2-(4-fluorophenoxy)phenyl]acetic acid 【CA登记号】 |
【 分 子 式 】C14H11FO3 【 分 子 量 】246.2379432 【元素组成】C 68.29% H 4.5% F 7.72% O 19.49% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 2-iodophenylacetic (I) with 4-fluorophenol (II) by means of K2CO3 in nitrobenzene al 160 C gives 2-(4-fluoophenoxy)phenylacetic acid (III), which by treatment with refluxing SOCl2 is converted to the corresponding acid chloride (IV). The cyclization of (IV) by means of AlCl3 in refluxing dichloroethane affords 2-fluoro-10,11-dihydro-11-oxodibenzo[b,f]oxepin (V), which is treated with 2-(dimethylamino)ethylthiol (VI) and boron trifluoride ethereate in acetic acid yielding 2-fluoro-11-[2-(dimethylamino)ethythio]dibenzo[b,f]oxepin (VII). The reaction of (VII) with phenyl chloro-formate (VIII) by means of K2CO3 in methylene chloride affords 2-fluoro-11-[2-(N-methyl-N-phenyloxycarbonylamino)ethythio]dibenzo[b,f]oxepin (IX), which is finally hydrolyzed with KOH-ethylene glycol al 155 C.
| 【1】 Morales-Alanis, H.; et al.; Antiandrogenic activity of a series of des-A-steroid derivatives. J Med Chem 1985, 28, 12, 1796. |
| 【2】 Anderson, V.B.; Ong, H.H.; Profitt, J.A. (Aventis SA); Aminoalkylthiobenzoxepines, process for their preparation as well as pharmaceutical compsns. containing them. JP 7995583 . |
| 【3】 Castaner, J.; Prous, J.; Fluradoline hydrochloride. Drugs Fut 1985, 10, 10, 813. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 27337 | 2-(2-iodophenyl)acetic acid | 18698-96-9 | C8H7IO2 | 详情 | 详情 |
| (II) | 19639 | 4-fluorophenol | 371-41-5 | C6H5FO | 详情 | 详情 |
| (III) | 27338 | 2-[2-(4-fluorophenoxy)phenyl]acetic acid | C14H11FO3 | 详情 | 详情 | |
| (IV) | 27339 | 2-[2-(4-fluorophenoxy)phenyl]acetyl chloride | C14H10ClFO2 | 详情 | 详情 | |
| (V) | 27340 | 8-fluorodibenzo[b,f]oxepin-10(11H)-one | C14H9FO2 | 详情 | 详情 | |
| (VI) | 27341 | 2-(dimethylamino)ethylhydrosulfide | 13242-44-9 | C4H11NS | 详情 | 详情 |
| (VII) | 27342 | N-[2-[(8-fluorodibenzo[b,f]oxepin-10-yl)sulfanyl]ethyl]-N,N-dimethylamine | C18H18FNOS | 详情 | 详情 | |
| (VIII) | 13580 | 1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate | 1885-14-9 | C7H5ClO2 | 详情 | 详情 |
| (IX) | 27343 | phenyl 2-[(8-fluorodibenzo[b,f]oxepin-10-yl)sulfanyl]ethyl(methyl)carbamate | C24H20FNO3S | 详情 | 详情 |