Facile synthesis of 2-bromo-3-fluorobenzonitrile: An application and study of the halodeboronation of aryl boronic acids

被引：58

作者：

Szumigala, RH ^{[1
]}

Devine, PN ^{[1
]}

Gauthier, DR ^{[1
]}

Volante, RP ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 02期

关键词：

D O I：

10.1021/jo035184p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A scaleable synthesis of 2-bromo-3-fluorobenzonitrile via the NaOMe-catalyzed bromodeboronation of 2-cyano-6-fluorophenylboronic acid was developed. The generality of this transformation was demonstrated through the halodeboronation of a series of aryl boronic acids. Both aryl bromides and aryl chlorides were formed in good to excellent yields when the corresponding aryl boronic acid was treated with 1,3-dihalo-5,5-dimethylhydantoin and 5 mol % NaOMe.

引用

页码：566 / 569

页数：4

共 37 条

[1] Studies of the boron-carbon linkage Part I The oxidation and nitration of phenylboric acid
Ainley, AD
Challenger, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1930, : 2171 - 2180
[2] REGIOSELECTIVE FUNCTIONALIZATION IN 2 POSITION OF 1,3-DISUBSTITUTED BENZENES
BENNETAU, B
RAJARISON, F
DUNOGUES, J
BABIN, P
[J]. TETRAHEDRON, 1993, 49 (47) : 10843 - 10854
[3] Black WC, 1998, SYNTHESIS-STUTTGART, P1101
[4] STEREOSPECIFIC CONVERSION OF ALKENYLBORONIC ACIDS INTO ALKENYL BROMIDES WITH INVERSION OF CONFIGURATION - STRIKING DIFFERENCES IN STEREOCHEMISTRY OF REPLACEMENT OF BORONIC ACID SUBSTITUENT BY BROMINE AND IODINE AND ITS SIGNIFICANCE IN TERMS OF REACTION-MECHANISM
BROWN, HC
HAMAOKA, T
RAVINDRA.N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (19) : 6456 - 6457
[5] Directed ortho metalation of neopentyl benzoates with LDA: Preparation of arylboronic acids
Caron, S
Hawkins, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2054 - 2055
[6] Electrophilic ipso substitution of trimethylsilyl groups in fluorobenzenes
Coe, PL
Stuart, AM
Moody, DJ
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1998, 92 (01) : 27 - 32
[7] DIA C, 2001, J AM CHEM SOC, V123, P2719
[8] REGIOSPECIFIC SYNTHESIS OF MONO DERIVATIVES AND POLYIODO DERIVATIVES OF BENZENE
FELIX, G
DUNOQUES, J
PISCIOTTI, F
CALAS, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (07): : 488 - 488
[9] Hudlicky M., 1983, CHEM FUNCTIONAL GROU, P1021
[10] SYNTHESIS OF ARYL HALIDES VIA ORGANOBORANE CHEMISTRY
KABALKA, GW
SASTRY, KAR
SASTRY, U
SOMAYAJI, V
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1982, 14 (05) : 359 - 362

← 1 2 3 4 →