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HRID 248136作成日:2026年10月23日

1,3-Dibromobenzene → 3-Bromobiphenyl

https://huagongshe.com/ja/reaction/248136

反応式

関与物質

役割名称HCID仕込み量
反応物1,3-DibromobenzeneHCID 7927—
反応物Sodium CarbonateHCID 10340—
反応物IodobenzeneHCID 11575—
反応物Sodium HydroxideHCID 14798—
反応物Triisopropyl borateHCID 21531—
反応物Boronic AcidHCID 61668—
反応物ButyllithiumHCID 178418339—
触媒HCID 178418397HCID 178418397—
溶媒TolueneHCID 1140—
溶媒Diethyl EtherHCID 3283—
溶媒TetrahydrofuranHCID 8028—
生成物3-BromobiphenylHCID 16449—

反応手順

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##

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US05208329
出典データセットuspto-grants-1993_05
ORD IDord-c162315141934898b8ef634f75735e1c
出典メモuspto-grants-1993_05