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【结 构 式】 
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【分子编号】60514 【品名】4,5-dibromo-6-[3-(4-chlorophenyl)propoxy]-3(2H)-pyridazinone 【CA登记号】 |
【 分 子 式 】C13H11Br2ClN2O2 【 分 子 量 】422.50332 【元素组成】C 36.96% H 2.62% Br 37.82% Cl 8.39% N 6.63% O 7.57% |
合成路线1
该中间体在本合成路线中的序号：(I)The title compound was prepared by condensation of the dibromopyridiazinone (I) with 3-picolylamine (II), followed by conversion to the corresponding hydrochloride salt
| 【1】 Tanikawa, K.; Saito, A.; Matsumoto, T.; Sakoda, R.; Tsuruzoe, N.; Shikada, K.-I. (Nissan Chemical Industry, Ltd.); Pyridazinone deriv.. EP 0482208; JP 1992507543; US 5202323; US 5314883; US 5318968; WO 9116314 . |
合成路线2
该中间体在本合成路线中的序号：(I)An improved procedure, amenable to the industrial synthesis of the precursor (I) was further developed. Heck coupling of p-chloroiodobenzene (III) with allyl alcohol (IV) in the presence of tetramethylammonium chloride and a catalytic amount of palladium acetate provided 3-(p-chlorophenyl)propanal (V) along with minor amounts of its branched isomer (VI). Further reduction of this mixture with NaBH4 led to the respective alcohols (VII) and (VIII). Only the desired alcohol (VII) underwent bromination to the desired bromide (IX) in the presence of PBr3 in hot toluene, whereas the branched alcohol (VIII) was dehydrohalogenated to olefin (X). Subsequent alkylation of pyridazinedione (XI) with the above reaction mixture afforded the pure intermediate
| 【1】 Matsumoto, H.; Kamikawaji, M.; Horiuchi, T. (Nissan Chemical Industry, Ltd.); Processes for the preparation of (p-chlorophenyl)propanol derivs.. EP 1138660; WO 0035843 . |
| 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) | 60514 | 4,5-dibromo-6-[3-(4-chlorophenyl)propoxy]-3(2H)-pyridazinone | C13H11Br2ClN2O2 | 详情 | 详情 | |
| (III) | 19395 | 1-chloro-4-iodobenzene | 637-87-6 | C6H4ClI | 详情 | 详情 |
| (IV) | 12234 | 2-Propen-1-ol; Allyl alcohol | 107-18-6 | C3H6O | 详情 | 详情 |
| (V) | 60515 | 3-(4-chlorophenyl)propanal | C9H9ClO | 详情 | 详情 | |
| (VI) | 60516 | 2-(4-chlorophenyl)propanal | C9H9ClO | 详情 | 详情 | |
| (VII) | 60517 | 3-(4-chlorophenyl)-1-propanol | C9H11ClO | 详情 | 详情 | |
| (VIII) | 60518 | 2-(4-chlorophenyl)-1-propanol | C9H11ClO | 详情 | 详情 | |
| (IX) | 60520 | 1-(3-bromopropyl)-4-chlorobenzene | C9H10BrCl | 详情 | 详情 | |
| (X) | 60519 | 1-chloro-4-isopropenylbenzene | C9H9Cl | 详情 | 详情 | |
| (XI) | 63949 | 4,5-dibromo-1,2-dihydro-3,6-pyridazinedione | C4H2Br2N2O2 | 详情 | 详情 |