Vanillin → 4-[(2-Fluorobenzyl)oxy]-3-methoxybenzaldehyde

HRID 2218552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2218552
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:20][C:19]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[O:11][CH3:10]

Komponenten

5

Edukt 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotoluene

Produkt 1

HCID 7354584-[(2-Fluorobenzyl)oxy]-3-methoxybenzaldehydeAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

0.5M solution of 1-bromomethyl-2-fluoro-benzene (1.5 mg, 8 mmol) in DMF was added dropwise to a suspension of 3-methoxy-4-hydroxy-benzaldehyde (1.1 g, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (120 mg, 7.3 mmol) in DMF (100 ml). The reaction mixture was treated as described in Example 4. The residue was purified on silica gel, obtaining 1.89 g (quantitative yield) of the title compound, yield 100%.

Aufarbeitung

  1. additionThe reaction mixture was treated
  2. customThe residue was purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-73d9aac700084d7caf32eb5a268a945d
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411091B2

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