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【结 构 式】 
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【分子编号】39756 【品名】ethyl 3-bromo-4-hydroxybenzoate 【CA登记号】 |
【 分 子 式 】C9H9BrO3 【 分 子 量 】245.07266 【元素组成】C 44.11% H 3.7% Br 32.6% O 19.59% |
合成路线1
该中间体在本合成路线中的序号：(II)Bromination of ethyl 4-hydroxybenzoate (I) by means of N-bromosuccinimide and HBF4.Et2O produced ethyl 3-bromo-4-hydroxybenzoate (II), which was further iodinated to (III) employing I2 and K2CO3. Subsequent condensation of (III) with ethylene glycol under Mitsunobu conditions afforded (hydroxyethyl)ether (IV). Palladium-catalyzed coupling of (IV) with 3-chlorophenylboronic acid (V) gave rise to terphenyl derivative (VI). Amide (VII) was then obtained by treatment of ester (VI) with n-dodecylamine in the presence of butyllithium. Finally, alcohol (VII) oxidation using N-methylmorpholine-N-oxide and tetrapropylammonium perruthenate furnished the title carboxylic acid.
| 【1】 Butera, J.A.; Caufield, C.E.; Greenfield, A.; Gundersen, E.G.; Lennox, J.R.; Graceffa, R.F.; Mayer, S.C.; Katz, A.H.; McDevitt, R.E.; Havran, L.M. (American Home Products Corp.); 2,3,5-Substd. biphenyls useful in the treatment of insulin resistance and hyperglycemia. WO 9961410 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40735 | 1-dodecanamine; dodecylamine | 124-22-1 | C12H27N | 详情 | 详情 | |
| (I) | 13492 | ethyl p-hydroxybenzoate; ethyl 4-hydroxybenzoate | 120-47-8 | C9H10O3 | 详情 | 详情 |
| (II) | 39756 | ethyl 3-bromo-4-hydroxybenzoate | C9H9BrO3 | 详情 | 详情 | |
| (III) | 39757 | ethyl 3-bromo-4-hydroxy-5-iodobenzoate | C9H8BrIO3 | 详情 | 详情 | |
| (IV) | 39758 | ethyl 3-bromo-4-(2-hydroxyethoxy)-5-iodobenzoate | C11H12BrIO4 | 详情 | 详情 | |
| (V) | 39759 | 3-chlorophenylboronic acid | 63503-60-6 | C6H6BClO2 | 详情 | 详情 |
| (VI) | 39760 | C23H20Cl2O4 | 详情 | 详情 | ||
| (VII) | 39761 | C33H41Cl2NO3 | 详情 | 详情 |