Bromine → HCID 18613734, Verbindung

HRID 1264910Notizen

Reaktionsgleichung

[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C>[Br:26][CH:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A suspension of the quinazolinone (17) (50.0 g, 0.56 mmol) and anhydrous sodium acetate (56 mg) in glacial acetic acid (1.0 mL) was heated to 40° C. and treated dropwise with a solution of bromine (90 mg, 0.56 mmol) in glacial acetic acid (5 mL). Once the starting material was fully consumed by TLC analysis, the mixture was poured onto water (5 mL), basified with saturated aqueous sodium hydrogen carbonate and extracted with tert-butylmethyl ether. The combined organic phases were dried (MgSO4), filtered, and concentrated to a solid which was purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, v/v] to give the title bromide (18) (166 mg, 85%) as an off white solid:

Aufarbeitung

customOnce the starting material was fully consumed by TLC analysis
additionthe mixture was poured onto water (5 mL)
extractionextracted with tert-butylmethyl ether
dry with materialThe combined organic phases were dried (MgSO4)
filtrationfiltered
concentrationconcentrated to a solid which
customwas purified by silica-gel column chromatography [eluent

Quellen und Nachweise

ORD-Eintrag: ord-9c5a14bf72f64e0bb9dc9b9ddf6a0062
Quelldatensatz: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06545005B1

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