1,3-Dibromobenzene → 3-Bromobiphenyl

HRID 248136

反応式

HRID 248136 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.B(O)O.C([Li])CCC.B(OC(C)C)(OC(C)C)OC(C)C.[OH-].[Na+].I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CCOCC.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:4]1[CH:3]=[C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:7]=[CH:6][CH:5]=1

参加物

12

反応物 7

HCID 79271,3-Dibromobenzene2 回HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 14798Sodium HydroxideHCID 21531Triisopropyl borateHCID 61668Boronic Acid2 回HCID 178418339Butyllithium

生成物 1

HCID 164493-Bromobiphenyl

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Starting with readily available starting materials, 1,3-dibromobenzene and the appropriately substituted iodobenzene, it is possible to prepare biphenyls having 3', 4' and 5' position substitution. Referring to Flow Sheet AE 1,3-dibromobenzene AE1 is converted to boronic acid AE2 by first reacting with butyl lithium in anhydrous THF or ether at about -78° C. followed by addition of triisopropyl borate. The resultant intermediate is worked up with sodium hydroxide and acidified. Boronic acid AE2 is subsequently reacted with the appropriate iodobenzene AE3 in toluene and aqueous sodium carbonate with tetrakistriphenylphosphinepalladium as a catalyst to produce the 3-bromo biphenyl B1. This reaction to B1 is well known in art with reference made herein to N. Miyaura, T. Yanagi and A. Suzuki, Syn. Comm., 11, 513 (1981). ##STR19##

出典と根拠

ORDレコード
ord-c162315141934898b8ef634f75735e1c
出典データセット
uspto-grants-1993_05
特許番号
US05208329

関連ノート

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