HRID1475926

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6326

Ethyne

C2H2

2 次

HCID282071

3-Iodophthalic anhydride

C8H3IO3

HCID15263377

5-Iodo-2-benzofuran-1,3-dione

C8H3IO3

结构：O=C1OC(=O)c2cc(C#Cc3ccc4c(c3)C(=O)OC4=O)ccc21

HCID58986478

5,5'-(1,2-Ethynediyl)bis-(1,3-Isobenzofurandione)

C18H6O6

PRODUCTS

生成物

HCID58986478

5,5'-(1,2-Ethynediyl)bis-(1,3-Isobenzofurandione)

C18H6O6

结构：O=C1OC(=O)c2c(C#Cc3cccc4c3C(=O)OC4=O)cccc21

HCID88962226

未命名化合物

PROCEDURE

实验过程

The present inventors have found that (ethyne-1,2-diyl)bis(isobenzofuran-1,3-diones), such as 5,5′-(ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione), may be obtained in a high yield in a one-step procedure by employing a Sonogashira coupling to react a chloro-, bromo-, or iodoisobenzofuran-1,3-dione, such as 5-chloro-, 5-bromo-, or 5-iodoisobenzofuran-1,3-dione, with acetylene, i.e. ethyne. By employing a one step procedure and by avoiding aqueous work-up, causing hydrolysis of the anhydride moieties, a (ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione), such as 5,5′-(ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione), may be obtained in significantly higher yield and shorter process time compared to known processes.

WORKUP

后处理

customa high yield in a one-step procedure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5a7952cc93f641d8be0157c3cbfd42bf
来源数据集: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09018401B2
来源说明: uspto-grants-2015_04

反应 SMILES

I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=[O:11].I[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[O:18][C:17]2=[O:24].C#C.[C:27]([C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[C:45](=[O:49])[O:44][C:43]2=[O:50])#[C:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:38])[O:33][C:32]2=[O:39]>>[C:27]([C:21]1[CH:22]=[CH:14][CH:15]=[C:16]2[C:20]=1[C:19](=[O:23])[O:18][C:17]2=[O:24])#[C:28][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=[O:11].[C:28]([C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:38])[O:33][C:32]2=[O:39])#[C:27][C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[C:45](=[O:49])[O:44][C:43]2=[O:50]