Acetylene → 5,5'-(1,2-Ethynediyl)bis-(1,3-Isobenzofurandione)
Reaction equation
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]Participants
6
Procedure
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
- customa high yield in a one-step procedure
Sources & evidence
- ORD record
- ord-5a7952cc93f641d8be0157c3cbfd42bf
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018401B2
Reaction notes
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