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【结 构 式】 
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【分子编号】50505 【品名】4,4'-Dichlorobenzhydrol; Bis(4-chlorophenyl)carbinol 【CA登记号】90-97-1 |
【 分 子 式 】C13H10Cl2O 【 分 子 量 】253.1272 【元素组成】C 61.69% H 3.98% Cl 28.01% O 6.32% |
合成路线1
该中间体在本合成路线中的序号：(I)Condensation of 4,4'-dichlorobenzhydrol (I) with 2-bromoethanol (II) in the presence of sulfuric acid gave the bromopropyl ether (III), which was further condensed with 2-mercaptoethanol (IV), yielding thioether (V). Subsequent coupling of alcohol (V) with methyl 3-(4-hydroxyphenyl)propionate (VI) under Mitsunobu conditions furnished adduct (VII). Basic hydrolysis of the methyl ester function generated acid (VIII). After conversion of (VIII) to the corresponding acid chloride, its condensation with trifluoroacetic anhydride gave rise to the trifluoromethyl ketone (IX). The sulfide group of (X) was finally oxidized to the title sulfone using meta-chloroperbenzoic acid.
| 【1】 Banville, J.; Burke, J.R.; Gai, Y.; Johnson, G.; Zusi, F.C. (Bristol-Myers Squibb Co.); Selective cPLA2 inhibitors. EP 1140791; WO 9915129 . |
| 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) | 50505 | 4,4'-Dichlorobenzhydrol; Bis(4-chlorophenyl)carbinol | 90-97-1 | C13H10Cl2O | 详情 | 详情 |
| (II) | 10059 | Ethylene bromohydrin; 2-Bromo-1-ethanol | 540-51-2 | C2H5BrO | 详情 | 详情 |
| (III) | 50506 | 1-[(2-bromoethoxy)(4-chlorophenyl)methyl]-4-chlorobenzene; bis(4-chlorophenyl)methyl 2-bromoethyl ether | C15H13BrCl2O | 详情 | 详情 | |
| (IV) | 36375 | 2-Sulfanyl-1-ethanol; 2-Mercaptoethanol | 60-24-2 | C2H6OS | 详情 | 详情 |
| (V) | 50507 | 2-([2-[bis(4-chlorophenyl)methoxy]ethyl]sulfanyl)-1-ethanol | C17H18Cl2O2S | 详情 | 详情 | |
| (VI) | 30341 | methyl 3-(4-hydroxyphenyl)propanoate; 4-Hydroxyphenylpropionic acid methyl ester; 3-(4-Hydroxyphenyl)propionic acid methyl ester | 5597-50-2 | C10H12O3 | 详情 | 详情 |
| (VII) | 50508 | methyl 3-[4-[2-([2-[bis(4-chlorophenyl)methoxy]ethyl]sulfanyl)ethoxy]phenyl]propanoate | C27H28Cl2O4S | 详情 | 详情 | |
| (VIII) | 50509 | 3-[4-[2-([2-[bis(4-chlorophenyl)methoxy]ethyl]sulfanyl)ethoxy]phenyl]propionic acid | C26H26Cl2O4S | 详情 | 详情 | |
| (IX) | 50510 | 4-[4-[2-([2-[bis(4-chlorophenyl)methoxy]ethyl]sulfanyl)ethoxy]phenyl]-1,1,1-trifluoro-2-butanone | C27H25Cl2F3O3S | 详情 | 详情 |