Dimethylformamide → Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

HRID 1295921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295921
[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13](=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20].CN(C)[CH:24]=[O:25]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([O:25][CH2:24][CH3:13])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][CH3:20])=[O:8]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2439345-bromo-2-hydroxy-4-methylbenzoic acid

Produkt 1

HCID 22929763Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

After dissolving 5-bromo-2-hydroxy-4-methylbenzoic acid (9.35 g) in dimethylformamide, potassium carbonate (14 g) and ethyl iodide (8 ml) were added in that order and the mixture was stirred at 50° C. for 3 hours. It was then diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to yield ethyl 5-bromo-2-ethoxy-4-methylbenzoate. The product was dissolved in ethanol (100 ml), 5 N sodium hydroxide (20 ml) was added and the mixture was heated to reflux for 30 minutes. After adding 5 N hydrochloric acid (25 ml) for neutralization, extraction was performed with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (10.4 g) as a white solid.

Aufarbeitung

  1. additionwere added in that order
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a77b0601025942b6bf398b731656b7d4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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