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Synlett 2014; 25(13): 1896-1900
DOI: 10.1055/s-0034-1378352
DOI: 10.1055/s-0034-1378352
letter
Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes
Further Information
Publication History
Received: 05 April 2014
Accepted after revision: 28 May 2014
Publication Date:
01 July 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201413/lookinside/thumbnails/10.1055-s-0034-1378352-1.jpg)
Abstract
Manganese dioxide mediated oxidative cleavage of 1,3-disubstituted benzo[c]furans in dichloromethane at room temperature gave good yields of 1,2-di(het)aroylbenzenes.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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References and Notes
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- 14 1,2-Phenylenebis(2-thienylmethanone) (2a); Typical Procedure MnO2 (0.57 g, 7.09 mmol) was added to a stirred solution of benzo[c]furan 1a (0.5 g, 1.77 mmol) in CH2Cl2 (20 mL), and the mixture was stirred at r.t until the benzo[c]furan was consumed (~4 h). The mixture was then filtered through Celite and the residue was washed with CH2Cl2 (2 × 10 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel; 5% EtOAc–hexane) to give a brown solid; yield: 0.48 g (92%); mp 150–152 °C (Lit. see ref. 1b 149–150 °C); IR (KBr): 1623, 1582, 1568, 1514, 1416 cm–1; 1H NMR (300 MHz, CDCl3): δ = 7.66–7.64 (m, 2 H, ArH), 7.58–7.56 (m, 4 H, ArH), 7.39–7.38 (m, 2 H, ArH), 6.99–6.96 (m, 2 H, ArH); 13C NMR (75 MHz, CDCl3): δ = 188.3, 144.0, 139.4, 135.1, 135.0, 130.6, 129.2, 128.1; DEPT-135 (75 MHz, CDCl3): δ = 135.2, 135.0, 130.6, 129.2, 128.1; HRMS (EI): m/z [M+] calcd for C16H10O2S2: 298.0122; found: 298.0121.