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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 34021Erstellt: 25. Oktober 2026

Dimethylformamide → 5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehyde

https://huagongshe.com/reaction/34021

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDimethylformamideHCID 6228—
EduktDiisopropylamineHCID 7912—
Edukt(6-Bromo-2,3-difluorophenyl)trimethylsilaneHCID 23070109—
LösungsmittelWaterHCID 962—
LösungsmittelTetrahydrofuranHCID 8028—
LösungsmittelHexaneHCID 8058—
LösungsmittelEthyl AcetateHCID 8857—
Produkt5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehydeHCID 23070176—

Reaktionsbedingungen

Temperatur-78 °C

Reaktionsschritte

Under nitrogen atmosphere, to a solution containing 6.34 mL of N,N-diisopropylamine in 100 mL of tetrahydrofuran, 26.4 mL of 1.57 Mn-butyllithium in hexane was added at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 10.0 g of (6-bromo-2,3-difluorophenyl)trimethylsilane in 100 mL of tetrahydrofuran was added dropwise, stirred at this temperature for 1 hour, then added dropwise with 2.92 mL of N,N-dimethylformamide, allowed to gradually warm to room temperature, and stirred fro 3 hours. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane), to afford 9.70 g of the title compound as a colorless oil.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07429609B2
Quelldatensatzuspto-grants-2008_09
ORD IDord-ffc56b65863d460a9838b0858a75ec3d
Quellennotizuspto-grants-2008_09