o-Chloroacetanilide → HCID 156594431, Verbindung

HRID 1490817

Reaktionsgleichung

Reaktionsgleichung von HRID 1490817
CC(=O)Nc1ccccc1Cl>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>CC(=O)Nc1cc(B2OC(C)(C)C(C)(C)O2)ccc1Cl.CC(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cc1Cl

Komponenten

7

Edukt 1

HCID 10777o-Chloroacetanilide

Produkt 2

HCID 130046623HCID 130046623, VerbindungAusbeute 35 %HCID 156594431HCID 156594431, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 165587889Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Following general procedure F using 2‐chloroacetanilide (42.4 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1.1 meta:para borylation in 74% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐6:4) to give the title compound (as a 1:1.3:0.4 mixture of meta:para:SM ratio, as determined by 1 H NMR) as a colourless oil. NMR yields have been used for all comparisons.

Quellen und Nachweise

ORD-Eintrag
ord-364444f55747421995a80216950a4c51
Quelldatensatz
Borylation dataset from Roche

Verknüpfte Notizen

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