Benzyl Chloride → 2-(Benzyloxy)-4-fluorobenzaldehyde

HRID 18170

Reaktionsgleichung

Reaktionsgleichung von HRID 18170
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.O>CN(C=O)C>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27792684-Fluoro-2-hydroxybenzaldehydeHCID 22728543Water ethylacetate

Produkt 1

HCID 106809572-(Benzyloxy)-4-fluorobenzaldehydeAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-2-hydroxy-benzaldehyde (560 mg, 4 mmol) in DMF (10 ml) were added benzyl chloride (0.5 ml, 4.33 mmol), and K2CO3 (860 mg, 6.22 mmol). After heating at reflux for an hour, the reaction mixture was allowed to cool to room temperature and was poured into a mixture of EtOAc/H2O. The organic layer was separated, washed with H2O and dried over MgSO4. The resulting oil was purified by flash chromatography to give 2-benzyloxy-4-fluoro-benzaldehyde as pale oil (628 mg, 68%), 1H NMR (CDCl3, 300 MHz) δ: 5.17 (s, 2H), 6.74 (m, 2H), 7.36 (m, 5H), 7.88 (m, 1H), 10.51 (s, 1H).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for an hour
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. customThe resulting oil was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bab34257f35f44208f93b82c012ad71a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741326B2

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