2-bromo-6-methoxy-1,4-benzenediol -Drug Synthesis Database

【结构式】

【分子编号】56684

【品名】2-bromo-6-methoxy-1,4-benzenediol

【CA登记号】

【分子式】C₇H₇BrO₃

【分子量】219.03478

【元素组成】C 38.39% H 3.22% Br 36.48% O 21.91%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XVII)

Alternatively, the bis-methoxymethyl ether (XVIII), prepared from 2-bromo-6-methoxyhydroquinone (XVII), was subjected to palladium-catalyzed coupling with 9-decen-1-ol (XIX) to afford adduct (XX). After catalytic hydrogenation of olefin (XX), the resultant saturated alcohol (XXI) was oxidized to aldehyde (XXII) under Swern conditions. Wittig condensation of (XXII) with the phosphonium salt (XV) led to the heptadecenyl derivative (XXIII). Subsequent hydrolysis of the methoxymethyl ethers of (XXIII) by means of HBr in EtOH furnished the deprotected hydroquinone (XXIV). This was finally oxidized to the title quinone employing silver carbonate in benzene.

参考文献中间体

合成目标

【1】 Yadav, J.S.; et al.; A practical preparation of functionalized alkylbenzoquinones synthesis of maesanin and irisquinone. J Org Chem 1992, 57, 11, 3242.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	56682	heptyl(triphenyl)phosphonium bromide	13423-48-8	C₂₅H₃₀BrP	详情	详情
(XVII)	56684	2-bromo-6-methoxy-1,4-benzenediol		C₇H₇BrO₃	详情	详情
(XVIII)	56685	1-bromo-3-methoxy-2,5-bis(methoxymethoxy)benzene; 3-bromo-2,5-bis(methoxymethoxy)phenyl methyl ether		C₁₁H₁₅BrO₅	详情	详情
(XIX)	56686	9-Decen-1-ol; 9-Decene-1-ol; omega-Decen-1-ol; Trepanol; Decylenic alcohol	13019-22-2	C₁₀H₂₀O	详情	详情
(XX)	56687	(E)-10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]-9-decen-1-ol		C₂₁H₃₄O₆	详情	详情
(XXI)	56688	10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]-1-decanol		C₂₁H₃₆O₆	详情	详情
(XXII)	56689	10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]decanal		C₂₁H₃₄O₆	详情	详情
(XXIII)	56690	3-[(Z)-10-heptadecenyl]-2,5-bis(methoxymethoxy)phenyl methyl ether; 1-[(Z)-10-heptadecenyl]-3-methoxy-2,5-bis(methoxymethoxy)benzene		C₂₈H₄₈O₅	详情	详情
(XXIV)	56691	2-[(Z)-10-heptadecenyl]-6-methoxy-1,4-benzenediol		C₂₄H₄₀O₃	详情	详情

Extended Information