Methyl chloroacetate → 7-Bromo-5-fluorobenzofuran-2-carboxylic acid

HRID 535675

Reaktionsgleichung

Reaktionsgleichung von HRID 535675
Cl[CH2:2][C:3]([O:5]C)=[O:4].[Br:7][C:8]1[C:9]([OH:17])=[C:10]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH:11]=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>O1CCCC1.O>[Br:7][C:8]1[C:9]2[O:17][C:2]([C:3]([OH:5])=[O:4])=[CH:11][C:10]=2[CH:13]=[C:14]([F:16])[CH:15]=1

Komponenten

7

Edukt 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehyde

Produkt 1

HCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acidAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Methyl chloroacetate (7.6 mL, 86.8 mmol) was added to a mixture of 3-bromo-5-fluoro-2-hydroxy-benzaldehyde (9.5 g, 43.4 mmol), tetra-N-butyl-ammonium iodide (1.6 g, 4.34 mmol) and anhydrous potassium carbonate (24 g, 174 mmol). The reaction mixture was heated at 130° C. for 4 h, cooled to 0° C., diluted with tetrahydrofuran (100 mL) and then potassium hydroxide (17 g, 303 mmol) in water (100 mL). The mixture was stirred at rt for 18 h and then, concentrated under reduced pressure. The residue was acidified with HCl and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1) to give 7.0 g (63%) of the product.

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1)

Quellen und Nachweise

ORD-Eintrag
ord-5e519e47b4254bf38cafbd0db2f6a7ce
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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