Phenacyl bromide → Diazoacetophenone

HRID 1397369Notizen

Reaktionsgleichung

C1CCN2C(=NCCC2)CC1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C1(C)C=CC(S([NH:31][NH:32]S(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>C1COCC1>[N+:31](=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])=[N-:32]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

DBU (7.5 mL, 50.2 mmol) was added dropwise to a solution of 2-bromo-1-phenylethanone (2.0 g, 10.05 mmol) and N,N′-bis(p-toluenesulfonyl)hydrazine (6.8 g, 20.1 mmol) in dry THF (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, and quenched with aqueous saturated NaHCO3 solution. The organic product was extracted with EtOAc and the combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether) to get 2-diazo-1-phenylethanone (1.2 g, yield 82%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.78-7.76 (m, 2H), 7.56-7.53 (m, 1H), 7.48-7.43 (m, 2H), 5.91 (s, 1H).

Aufarbeitung

customquenched with aqueous saturated NaHCO3 solution
extractionThe organic product was extracted with EtOAc
washthe combined extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag: ord-32af7f05623242f4ae7b78ac9ed9fd28
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08901156B2

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