Improved process for chloroxidation of aryl sulfides to aryl sulfonyl chlorides in commercial grade formic acid

被引:14
作者
Wang, Chen [1 ]
Hamilton, Christopher [1 ]
Meister, Phillip [1 ]
Menning, Catherine [1 ]
机构
[1] Dow Chem Co USA, Midland, MI 48674 USA
关键词
D O I
10.1021/op0602223
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This paper discusses the process advantages of using commercial grade formic acid as the solvent for chlorine gas oxidation of aryl sulfides to sulfonyl chlorides. Compared to chloroxidation in methylene chloride, the chloroxidation in formic acid gave a consistently higher yield and easy product isolation for a sulfonyl chloride intermediate which was used in the production of the sulfonamide herbicide, penoxsulam.
引用
收藏
页码:52 / 55
页数:4
相关论文
共 16 条
[1]  
ARNDT K, 2003, Patent No. 6645918
[2]   THE CLEAVAGE OF ORGANIC SULFIDES WITH CHLORINE [J].
BAKER, RH ;
DODSON, RM ;
RIEGEL, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (12) :2636-2639
[3]   Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The "DCAT route" to thiophenesulfonamides [J].
Conrow, RE ;
Dean, WD ;
Zinke, PW ;
Deason, ME ;
Sproull, SJ ;
Dantanarayana, AP ;
DuPriest, MT .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (02) :114-120
[4]  
CREMLYN R, 1996, ORGANOSULFUR CHEM IN
[5]   SULFINYL AND SULFONYL CHLORIDES BY CHLORINATION [J].
DOUGLASS, IB ;
THOMAS, EG ;
FARAH, BS .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06) :1996-&
[6]   SOME NOVEL SULFONAMIDES - CHLOROSULFONATION OF ARYL ALKYL SULFIDES [J].
GOLDKAMP, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1780-&
[7]   KINETICS OF THE REACTION OF CHLORINE WITH FORMIC-ACID IN AQUEOUS SULFURIC-ACID [J].
HOQ, MF ;
INDU, B ;
ERNST, WR ;
NEUMANN, HM .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (02) :681-683
[8]  
HUDLICKY M, 1990, ACS MONOGR SER, V186, P250
[9]  
Hughes D. T. D., 1997, SULFONAMIDES ANTIBIO, P460
[10]  
Humffray A. A., 1981, J CHEM SOC P2, V2, P382