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【结 构 式】

【分子编号】32354

【品名】2-(bromomethyl)-4-methoxyphenyl methyl ether; 2-(bromomethyl)-1,4-dimethoxybenzene

【CA登记号】

【 分 子 式 】C9H11BrO2

【 分 子 量 】231.08914

【元素组成】C 46.78% H 4.8% Br 34.58% O 13.85%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The formylation of 1,4-dimethoxybenzene (I) with C6H11-Li, TMEDA and DMF gives 2,5-dimethoxybenzaldehyde (II), which is reduced with NaBH4 to the corresponding alcohol (III). The treatment of (III) with HBr affords the benzyl bromide (IV), which by reaction with PPh3 in hot toluene is converted into the phosphonium salt (V). The condensation of (V) with 5-formyl-2-hydroxybenzoic acid methyl ester (VI)(obtained by esterification of the corresponding acid (VII) with methanol and H2SO4) by means of LDA in THF affords the stilbene (VIII). Finally, this compound is reduced with H2 over Pd/C in ethyl acetate.

1 Kucerovy, A.; et al.; An efficient large-scale synthesis of methyl 5-[2-82,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoate. Org Process Res Dev 1997, 1, 4, 287.
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) 21946 1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether 150-78-7 C8H10O2 详情 详情
(II) 10174 2,5-Dimethoxybenzaldehyde 93-02-7 C9H10O3 详情 详情
(III) 32353 (2,5-dimethoxyphenyl)methanol 33524-31-1 C9H12O3 详情 详情
(IV) 32354 2-(bromomethyl)-4-methoxyphenyl methyl ether; 2-(bromomethyl)-1,4-dimethoxybenzene C9H11BrO2 详情 详情
(V) 32355 (2,5-dimethoxybenzyl)(triphenyl)phosphonium bromide C27H26BrO2P 详情 详情
(VI) 32356 methyl 5-formyl-2-hydroxybenzoate C9H8O4 详情 详情
(VII) 32357 5-Formylsalicylic acid; 5-formyl-2-hydroxybenzoic acid 616-76-2 C8H6O4 详情 详情
(VIII) 32358 methyl 5-[(E)-2-(2,5-dimethoxyphenyl)ethenyl]-2-hydroxybenzoate C18H18O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Improved large scale synthesis: The formylation of 1,4-dimethoxybenzene (I) with C6H11-Li, TMEDA and DMF gives 2,5-dimethoxybenzaldehyde (II), which is reduced with NaBH4 in toluene/methanol to the corresponding alcohol (III). The treatment of (III) with PBr3 in ethyl acetate affords the benzyl bromide (IV), which by reaction with dimethyl phosphite (IX) and NaH in toluene is converted into the phosphonate (X). The condensation of (X) with 5-formyl-2-hydroxybenzoic acid methyl ester (VI)(obtained by esterification of the corresponding acid (VII) with methanol and H2SO4) by means of LiHMDS in THF affords the stilbene (VIII). Finally, this compound is reduced with H2 over Pd/C in ethyl acetate.

1 Kucerovy, A.; et al.; An efficient large-scale synthesis of methyl 5-[2-82,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoate. Org Process Res Dev 1997, 1, 4, 287.
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) 21946 1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether 150-78-7 C8H10O2 详情 详情
(II) 10174 2,5-Dimethoxybenzaldehyde 93-02-7 C9H10O3 详情 详情
(III) 32353 (2,5-dimethoxyphenyl)methanol 33524-31-1 C9H12O3 详情 详情
(IV) 32354 2-(bromomethyl)-4-methoxyphenyl methyl ether; 2-(bromomethyl)-1,4-dimethoxybenzene C9H11BrO2 详情 详情
(VI) 32356 methyl 5-formyl-2-hydroxybenzoate C9H8O4 详情 详情
(VII) 32357 5-Formylsalicylic acid; 5-formyl-2-hydroxybenzoic acid 616-76-2 C8H6O4 详情 详情
(VIII) 32358 methyl 5-[(E)-2-(2,5-dimethoxyphenyl)ethenyl]-2-hydroxybenzoate C18H18O5 详情 详情
(IX) 32359 dimethyl phosphonate 868-85-9 C2H7O3P 详情 详情
(X) 32360 dimethyl 2,5-dimethoxybenzylphosphonate C11H17O5P 详情 详情
Extended Information