Ethyl Acetate → 5-Bromo-2-(2-fluoro-4-methoxyphenoxy)benzoic acid

HRID 335913

Reaktionsgleichung

Reaktionsgleichung von HRID 335913
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[C:12]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].CCOC(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:12]([O:10][C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[F:1])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 118912,5-Dibromobenzoic acidHCID 27745572-Fluoro-4-methoxyphenol

Produkt 1

HCID 574756385-Bromo-2-(2-fluoro-4-methoxyphenoxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A three-neck RBF equipped with a reflux condenser and overhead stirrer was charged with 2-fluoro-4-methoxyphenol (14.24 g, 100 mmol), 2,5-dibromobenzoic acid (25.5 g, 91 mmol), EtOAc (0.446 mL, 4.55 mmol), copper (I) triflate toluene complex (2:1) (0.484 g, 2.27 mmol) and toluene (300 mL). Cesium carbonate (59.4 g, 182 mmol) was carefully added portion-wise. The mixture was stirred for 10 minutes at RT then heated at 95° C. for 3 hours. The toluene was cooled to RT then extracted twice with 300 ml of water. The combined water extracts were acidified with 6 N HCl at which time a precipitate formed. The mixture was extracted with EtOAc (3×500 mL) and the combined organic fractions were dried over sodium sulfate and concentrated in vacuo. The resulting solid was triturated with minimal 1:1 Hexanes:EtOAc and filtered. The collected solid was dried in vacuo to afford 5-bromo-2-(2-fluoro-4-methoxyphenoxy)benzoic acid as a grey solid. The mother liquors were set aside for later recrystallizatio. MS m/z=341.0 [M+H].

Aufarbeitung

  1. customA three-neck RBF equipped with a reflux condenser and overhead stirrer
  2. temperaturethen heated at 95° C. for 3 hours
  3. extractionthen extracted twice with 300 ml of water
  4. customformed
  5. extractionThe mixture was extracted with EtOAc (3×500 mL)
  6. dry with materialthe combined organic fractions were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was triturated with minimal 1:1 Hexanes
  9. filtrationEtOAc and filtered
  10. customThe collected solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c6014187a184102861b820fe5ea691e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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