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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 248136Erstellt: 23. Oktober 2026

1,3-Dibromobenzene → 3-Bromobiphenyl

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

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,3-DibromobenzeneHCID 7927—
EduktSodium CarbonateHCID 10340—
EduktIodobenzeneHCID 11575—
EduktSodium HydroxideHCID 14798—
EduktTriisopropyl borateHCID 21531—
EduktBoronic AcidHCID 61668—
EduktButyllithiumHCID 178418339—
KatalysatorHCID 178418397HCID 178418397—
LösungsmittelTolueneHCID 1140—
LösungsmittelDiethyl EtherHCID 3283—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt3-BromobiphenylHCID 16449—

Reaktionsschritte

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##

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05208329
Quelldatensatzuspto-grants-1993_05
ORD IDord-c162315141934898b8ef634f75735e1c
Quellennotizuspto-grants-1993_05