4-bromo-N,N-dimethylbenzamide → 1-(4-Bromophenyl)-N,N-dimethylmethanamine

HRID 1484223

Reaktionsgleichung

C[SiH](C)C1C=CC=CC=1[SiH](C)C.[CH3:13][N:14]([CH3:24])[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:24][N:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=1)[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, 1,2-bis(dimethylsilyl)benzene (475 μL) was added through a syringe, and N,N-dimethyl-4-bromobenzamide (228 mg, 1.0 mmol) was added. The solution was stirred at 100° C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (20/1) as developing solvent, obtaining N,N-dimethyl-4-bromobenzylamine (184 mg, 0.86 mmol, 86%). The results are shown as Entry 2 in Table 5. The resulting amine was identified for geometry by 1H and 13C-NMR spectroscopy and IR spectroscopy.

Aufarbeitung

customA 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer
temperaturewas heat
customdried
customwas purged with argon atmosphere
distillationToluene was distilled off in vacuum
customThe crude product was purified by silica gel-

Quellen und Nachweise

ORD-Eintrag: ord-6598e394847d4a7c8a5a59d72926b71f
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09421532B2

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