4-Bromo-2-fluorobenzaldehyde → 4-Bromo-2-methoxybenzaldehyde

HRID 510636

Reaktionsgleichung

Reaktionsgleichung von HRID 510636
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[CH3:11][O-:12].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:12][CH3:11])[CH:3]=1

Komponenten

4

Edukt 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Produkt 1

HCID 110530414-Bromo-2-methoxybenzaldehydeAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-bromo-2-fluorobenzaldehyde (96%, 3.38 g, 16.0 mmol) in methanol (35 mL) at ambient temperature was added a 25 wt % solution of sodium methoxide in methanol (4.02 mL, 17.6 mmol), and the resulting solution was stirred and heated to reflux for 2 hours. The solution was cooled to ambient temperature and concentrated, and the residue was partitioned between dichloromethane (100 mL) and water (50 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 95/5 hexanes/ethyl acetate, to afford 4-bromo-2-methoxybenzaldehyde as a white solid (2.13 g, 62% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. customthe residue was partitioned between dichloromethane (100 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with 95/5 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a27d8079b7e54dac8ea973a5c9ec33c1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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