2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane -Drug Synthesis Database

【结构式】

【分子编号】51402

【品名】2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane

【CA登记号】4463-59-6

【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 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

This compound has been obtained in two related ways: 1. The reaction of 2-(2-bromoethoxy)anisole (I) with benzylamine (II) by heating at 80 C gives the secondary amine (III), which is condensed with epichlorohydrin (IV) by heating at 60 C to yield the isopropanol derivative (V). The condensation of (V) with 4-hydroxycarbazole (VI) by means of K2CO3 in refluxing dioxane affords the adduct (VII), which is finally debenzylated by hydrogenolysis with H2 over Pd/C in ethanol/water. 2. The condensation of the secondary amine (III) with 4-(2,3-epoxypropoxy)carbazole (VIII) in refluxing ethanol gives the already reported adduct (VII), which is debenzylated as indicated.

参考文献中间体

合成目标

【1】 Seres, P.; Cselenyak, J.; Nagy, K.; Simig, G.; Gregor, T.; Nagy, P.K.; Greff, Z.; Balazs, L.; Barkoczy, J.; Vereczkey, G.D.; Nemeth, N.; Szabo, T.; Ratkai, Z.; Doman, I. (Egis Pharmaceuticals Ltd.); Process and intermediates for preparing 1-[9'H-carbazol-4'-yloxy]-3-[2''-(2'''-methoxy-phenoxy)ethyl]amino]-propan-2-ol (carvedilol). EP 0918055 .

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)	51402	2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane	4463-59-6	C₉H₁₁BrO₂	详情	详情
(II)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(III)	30528	N-benzyl-2-(2-methoxyphenoxy)-1-ethanamine; N-benzyl-N-[2-(2-methoxyphenoxy)ethyl]amine		C₁₆H₁₉NO₂	详情	详情
(IV)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	51403	1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-chloro-2-propanol		C₁₉H₂₄ClNO₃	详情	详情
(VI)	29480	4-Hydroxycarbazole; 9H-carbazol-4-ol	52602-39-8	C₁₂H₉NO	详情	详情
(VII)	51404	1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)-2-propanol		C₃₁H₃₂N₂O₄	详情	详情
(VIII)	40171	9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole	51997-51-4	C₁₅H₁₃NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Guaiacol (I) was alkylated by means of boiling dibromoethane (II) to produce the bromoethyl ether (III). From this, the intermediate amine (VI) was prepared by Gabriel synthesis, via condensation with potassium phthalimide (IV) in hot DMF, followed by hydrazinolysis of the resultant N-substituted phthalimide (V).

参考文献中间体

合成目标

【1】 Lin, T.-H.; Chen, I.-J.; Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity. EP 1108710; WO 0005209 .

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)	13182	Guaiacol; 2-Methoxyphenol	90-05-1	C₇H₈O₂	详情	详情
(II)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(III)	51402	2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane	4463-59-6	C₉H₁₁BrO₂	详情	详情
(IV)	27890	Potassium phthalimide	1074-82-4	C₈H₄KNO₂	详情	详情
(V)	59617	2-[2-(2-methoxyphenoxy)ethyl]-1H-isoindole-1,3(2H)-dione		C₁₇H₁₅NO₄	详情	详情
(VI)	31105	2-(2-methoxyphenoxy)ethylamine; 2-(2-methoxyphenoxy)-1-ethanamine	1836-62-0	C₉H₁₃NO₂	详情	详情

Extended Information