5-(2-bromoacetyl)-2-hydroxybenzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】50873

【品名】5-(2-bromoacetyl)-2-hydroxybenzaldehyde

【CA登记号】

【分子式】C₉H₇BrO₃

【分子量】243.05678

【元素组成】C 44.47% H 2.9% Br 32.87% O 19.75%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The condensation of N-benzyl-N-[6-(4-phenylbutoxy)hexyl]amine (I) with 5-(bromoacetyl)salicylaldehyde (II) by means of TEA in isopropanol gives the adduct (III), which is debenzylated and reduced with H2 over Pt/C and Pd/C in ethanol to afford the target triol.

参考文献中间体

合成目标

【1】 Ariza Aranda, J.; Serra Masià, J.; Montserrat Vidal, C. (Laboratorios Salvat SA); 6-[4-(Phenylbutoxy)]hexylaminomethyl-4-hydroxy-alpha1,alpha3-benzenedimethanol. Process for obtaining it and novel intermediates for its preparation. ES 2065269 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	35837	N-benzyl-6-(4-phenylbutoxy)-1-hexanamine; N-benzyl-N-[6-(4-phenylbutoxy)hexyl]amine	C₂₃H₃₃NO	详情	详情
(II)	50873	5-(2-bromoacetyl)-2-hydroxybenzaldehyde	C₉H₇BrO₃	详情	详情
(III)	50874	5-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]acetyl)-2-hydroxybenzaldehyde	C₃₂H₃₉NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The condensation of 4-phenyl-1-butanol (I) with 1,6-dibromohexane (II) by means of NaH in THF gives the ether (III), which is condensed with benzylamine (IV) by means of NaI and TEA in DMSO to yield the secondary amine (V). The condensation of (V) with 5-(bromoacetyl)-2-hydroxybenzaldehyde (VI) in refluxing acetonitrile affords the tertiary amine (VII). The reduction of both carbonyl groups of (VII) by means of NaBH4 in methanol affords the dihydroxy amine (VIII), which is finally debenzylated by means of h2 over Pd/C in the same solvent to provide the target salmeterol. The intermediate 5-(bromoacetyl)-2-hydroxybenzaldehyde (VI) has been obtained by Friedel Crafts condensation of 2-hydroxybenzaldehyde (IX) with bromoacetyl chloride (X) by means of AlCl3 in dichloromethane.

参考文献中间体

合成目标

【1】 Rong, Y.; Ruoho, A.E.; A new synthetic approach to salmeterol. Synth Commun 1999, 29, 12, 2155.

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)	27291	4-phenyl-1-butanol	3360-41-6	C₁₀H₁₄O	详情	详情
(II)	24786	1,6-dibromohexane	629-03-8	C₆H₁₂Br₂	详情	详情
(III)	31479	1-[4-[(6-bromohexyl)oxy]butyl]benzene; 6-bromohexyl-4-phenylbutyl ether; 6-Bromohexyloxybutylbenzene	94749-73-2	C₁₆H₂₅BrO	详情	详情
(IV)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(V)	35837	N-benzyl-6-(4-phenylbutoxy)-1-hexanamine; N-benzyl-N-[6-(4-phenylbutoxy)hexyl]amine		C₂₃H₃₃NO	详情	详情
(VI)	50873	5-(2-bromoacetyl)-2-hydroxybenzaldehyde		C₉H₇BrO₃	详情	详情
(VII)	50874	5-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]acetyl)-2-hydroxybenzaldehyde		C₃₂H₃₉NO₄	详情	详情
(VIII)	35839	4-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]-1-hydroxyethyl)-2-(hydroxymethyl)phenol		C₃₂H₄₃NO₄	详情	详情
(IX)	21351	2-Hydroxybenzaldehyde;Salicylic aldehyde；2-Formylphenol;salicylaldehyde	90-02-8	C₇H₆O₂	详情	详情
(X)	27903	2-Bromoacetyl chloride	22118-09-8	C₂H₂BrClO	详情	详情

Extended Information