Water → Methyl 2-(3-bromo-4-methoxyphenyl)acetate

HRID 1420841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420841
CI.[Br:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10].[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10634081Methyl 2-(3-bromo-4-hydroxyphenyl)acetate

Produkt 1

HCID 12717575Methyl 2-(3-bromo-4-methoxyphenyl)acetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl iodide (2.05 mL, 4.68 g, 33 mmol) was added to a mixture of methyl 3-bromo-4-hydroxyphenylethanoate (Description 73, 7.35 g, 30 mmol) and potassium carbonate (8.29 g, 60 mmol) in dimethylformamide (30 mL) and the mixture was stirred at room temperature for 16 h. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with aqueous sodium hydroxide (1M, 2×100 mL), water (2×100 mL) and brine (100 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (7.65 g, 100%). 1H NMR (360 MHz, CDCl3) δ7.47 (1 H, d, J 2.1 Hz), 7.18 (1 H, dd, J 8.4, 2.1 Hz), 6.85 (1 H, d, J 8.4 Hz), 3.88 (3 H, s), 3.70 (3 H, s), and 3.49 (2 H, s).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic fractions were washed with aqueous sodium hydroxide (1M, 2×100 mL), water (2×100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b96a4f206ec94080a4bb1c17563404f0
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071927

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