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【结 构 式】 
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【分子编号】56243 【品名】2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenol 【CA登记号】 |
【 分 子 式 】C16H12I2O2 【 分 子 量 】490.07902 【元素组成】C 39.21% H 2.47% I 51.79% O 6.53% |
合成路线1
该中间体在本合成路线中的序号：(VI)Friedel-Crafts acylation of 2-methylbenzofuran (I) with p-anisoyl chloride (II) in the presence of SnCl4 afforded the benzoyl benzofuran derivative (III). Ketone (III) reduction to the corresponding benzyl benzofuran (IV) was accomplished employing either LiAlH4 or NaBH4 and ZnI2. The methyl ether group of (IV) was then cleaved with melted pyridine hydrochloride to give phenol (V). Aromatic iodination of (V) with either I2/KI or with ICl in morpholine led to the diiodo phenol (VI). This was then alkylated with ethyl bromoacetate (VII) to furnish ester (VIII), which was finally hydrolyzed with NaOH to the target carboxylic acid.
| 【1】 Singh, B.N.; Malm, J.; Mellin, C.; Li, Y.-L.; Nilsson, S.; Temciuc, M.; Carlsson, B.; Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J Med Chem 2002, 45, 3, 623. |
| 【2】 Norinder, U.; Bajorath, J.; Stearns, J.F. (Karo Bio AB); Receptor ligands. WO 9220331 . |
| 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) | 56239 | 2-Methylbenzofuran | C9H8O | 详情 | 详情 | |
| (II) | 22671 | 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride | 100-07-2 | C8H7ClO2 | 详情 | 详情 |
| (III) | 56240 | (4-methoxyphenyl)(2-methyl-1-benzofuran-3-yl)methanone | C17H14O3 | 详情 | 详情 | |
| (IV) | 56241 | 3-(4-methoxybenzyl)-2-methyl-1-benzofuran; methyl 4-[(2-methyl-1-benzofuran-3-yl)methyl]phenyl ether | C17H16O2 | 详情 | 详情 | |
| (V) | 56242 | 4-[(2-methyl-1-benzofuran-3-yl)methyl]phenol | C16H14O2 | 详情 | 详情 | |
| (VI) | 56243 | 2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenol | C16H12I2O2 | 详情 | 详情 | |
| (VII) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (VIII) | 56244 | ethyl 2-{2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy}acetate | C20H18I2O4 | 详情 | 详情 |