Water → 4-Bromo-2-(trifluoromethyl)benzaldehyde

HRID 415998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415998
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Br)Br)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C1C[O:18]CC1.O>[N+]([O-])([O-])=O.[Ag+].C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:18])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59474514Benzene, 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)-

Produkt 1

HCID 121872184-Bromo-2-(trifluoromethyl)benzaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)benzene (6.66 g, 16.8 mmol), silver nitrate (14.8 g, 87.3 mmol), THF (250 mL), and water (35 mL) in a 500 mL flask equipped with a magnetic stir bar, reflux condenser, and N2 inlet. Reflux the mixture while stirring for 2.5 hours then cool to room temperature. Filter the reaction through Celite®, add ethyl acetate (250 mL) and wash with water (2×200 mL) then saturated aqueous sodium chloride solution (1×200 mL). Dry over anhydrous magnesium sulfate, concentrate to an orange oil, and purify the crude product via silica gel chromatography eluting with hexanes to afford 3.46 g (81%) of the product as a clear oil: 1H NMR (300 MHz, CDCl3) δ 10.35-10.33 (m, 1H), 8.0 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=1.4 Hz), 7.86 (dd, 1H, J=1.2 Hz, J=8.3 Hz).

Aufarbeitung

  1. temperaturereflux condenser, and N2 inlet
  2. temperatureReflux the mixture
  3. filtrationFilter
  4. customthe reaction through Celite®
  5. washwash with water (2×200 mL)
  6. dry with materialDry over anhydrous magnesium sulfate
  7. concentrationconcentrate to an orange oil
  8. custompurify the crude product via silica gel chromatography
  9. washeluting with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4ce2748c2c844cc4a61beb76d4189b03
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088776B2

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