Ring formylation of bromobenzoate esters by direct metalation

被引:4
作者
Kende, AS [1 ]
Zhong, M [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
D O I
10.1080/00397919908085967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A study on the synthesis of a benzaldehyde containing an ester function directly from tert-butyl 4-lithiobenzate was described. t-Butyl 4-bromobenzoate reacted with butyllithium at -78 degrees C in THF, followed by immediate addition of DMF to give the desired benzaldehyde in moderate yield. The scope of this reaction was examined.
引用
收藏
页码:3401 / 3407
页数:7
相关论文
共 7 条
[1]   Stereoselective conjugate addition reactions of α,β-unsaturated tert-butyl esters with aryllithium reagents [J].
Frey, LF ;
Tillyer, RD ;
Caille, AS ;
Tschaen, DM ;
Dolling, UH ;
Grabowski, EJJ ;
Reider, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3120-3124
[2]  
Jones G., 1997, ORG REACTIONS, V49, P1
[3]  
LAMPE JW, 1994, J ORG CHEM, V59, P5417
[4]   THE METAL-PROMOTED FRIES REARRANGEMENT [J].
MILLER, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :322-323
[5]   HALOGEN-METAL EXCHANGE IN ESTERS OF HALOARYL ACIDS [J].
PARHAM, WE ;
JONES, LD .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (16) :2704-2706
[6]   Novel spirodihydrobenzofuranlactams as antagonists of endothelin and as inhibitors of HIV-1 protease produced by Stachybotrys sp. .2. Structure determination [J].
Roggo, BE ;
Hug, P ;
Moss, S ;
Stampfli, A ;
Kriemler, HP ;
Peter, HH .
JOURNAL OF ANTIBIOTICS, 1996, 49 (04) :374-379
[7]   Enantioselective 1,4-addition of aryllithium reagents to α,β-unsaturated tert-butyl esters in the presence of chiral additives [J].
Xu, F ;
Tillyer, RD ;
Tschaen, DM ;
Grabowski, EJJ ;
Reider, PJ .
TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1651-1655