|
【结 构 式】 
|
【分子编号】67827 【品名】4-bromo-3-(1,3-dioxolan-2-yl)phenol 【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：(III)Protection of 2-bromo-5-hydroxybenzaldehyde (I) as the corresponding ethylene ketal (III) by means of ethylene glycol (II) and p-TsOH in refluxing toluene, followed by coupling with 4-fluorobenzonitrile (IV) in the presence of K2CO3 in DMF and subsequent acetal hydrolysis with HCl in refluxing H2O/THF provides 4-(4-bromo-3-formylphenoxy) benzonitrile (V). Reduction of aldehyde (V) with NaBH4 in MeOH affords the benzylic alcohol (VI), which is then protected with DHP in the presence of CSA in CH2Cl2 to give the tetrahydropyranyl ether (VII). Finally, aryl bromide (VII) is submitted to halogen-metal exchange by treatment with BuLi, followed by borylation with (i-PrO)3B in THF and then treatment with HCl in refluxing H2O/THF .
| 【1】 Akama, T., Baker, S.J., Zhang, Y.K. et al. Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis. Bioorg Med Chem Lett 2009, 19(8): 2129-32. |
| 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) | 67826 | 2-bromo-5-hydroxybenzaldehyde | C7H5BrO2 | 详情 | 详情 | |
| (II) | 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 |
| (III) | 67827 | 4-bromo-3-(1,3-dioxolan-2-yl)phenol | C9H9BrO3 | 详情 | 详情 | |
| (IV) | 14144 | 4-Fluorobenzonitrile | 1194-02-1 | C7H4FN | 详情 | 详情 |
| (V) | 67828 | 4-(4-bromo-3-formylphenoxy)benzonitrile | C14H8BrNO2 | 详情 | 详情 | |
| (VI) | 67829 | 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile | C14H10BrNO2 | 详情 | 详情 | |
| (VII) | 67830 | 4-(4-bromo-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenoxy)benzonitrile | C19H18BrNO3 | 详情 | 详情 |