Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 1,3-Dibromobenzene | HCID 7927 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | Iodobenzene | HCID 11575 | — |
| Edukt | Sodium Hydroxide | HCID 14798 | — |
| Edukt | Triisopropyl borate | HCID 21531 | — |
| Edukt | Boronic Acid | HCID 61668 | — |
| Edukt | Butyllithium | HCID 178418339 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Diethyl Ether | HCID 3283 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 3-Bromobiphenyl | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US05208329 |
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| Quelldatensatz | uspto-grants-1993_05 |
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| ORD ID | ord-c162315141934898b8ef634f75735e1c |
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| Quellennotiz | uspto-grants-1993_05 |
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