Methyl iodide → 2-Bromo-7-methoxynaphthalene

HRID 1053788

Reaktionsgleichung

Reaktionsgleichung von HRID 1053788
CI.[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([OH:14])=[CH:11]2)=[CH:6][CH:5]=1.[C:15]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH:13]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6138277-Bromo-2-naphthol

Produkt 1

HCID 129927592-Bromo-7-methoxynaphthaleneAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl iodide (2 mL, 32.1 mmol) was added to a mixture of 7-bromonaphthalen-2-ol (6.26 g, 28.0 mmol) and K2CO3 (4.62 g, 33.4 mmol) in DMF (21 mL). After stirring for 3 days, the mixture was partitioned between ethyl acetate/H2O and the organic solution was further washed with H2O (5×60 mL). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (6.41 g, 96%).

Aufarbeitung

  1. customthe mixture was partitioned between ethyl acetate/H2O
  2. washthe organic solution was further washed with H2O (5×60 mL)
  3. dry with materialThe organic solution was then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5ad2b748e1924976b5b38648c9cd105a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394273B2

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