1005199-10-9Relevant articles and documents
Efficient method for synthesis of 2-acetylbenzo(b)thiophene and its derivatives, the key synthons for 5-lipoxygenase inhibitors
Chemburkar, Sanjay R.,Anderson, David G.,Reddy, Rajarathnam E.
, p. 1887 - 1894 (2010)
An efficient method was developed for synthesis of 2-acetylbenzo(b) thiophene (2a), the key intermediate for zileuton (1). Synthesis involves treatment of 2-chlorobenzaldehyde (5a) with tert-butylmercaptan (6) to form 2-(tert-butylthio)benzaldehyde (7a), which upon treatment with HBr in water gave the disulfide derivative 2,2'-disulfanediyldibenzaldehyde (8a) in 97% yield. Finally, the reaction of 8a with acetylacetone (9) and 1-chloroacetone (10) gave 2-acetylbenzo(b)thiophene (2a) in 94% yield. The methodology is general and suitable for the preparation of its derivatives, 2b-d. Copyright