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

HRID 335908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335908
[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]=[C:19]([F:21])[C:18]([Br:22])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C(OCC)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Br:22][C:18]1[C:19]([F:21])=[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 27745572-Fluoro-4-methoxyphenolHCID 673830652,5-Dibromo-4-fluorobenzoic acid

Produkt 1

HCID 673830755-Bromo-4-fluoro-2-(2-fluoro-4-methoxyphenoxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A 2 L RB flask was charged with 2-fluoro-4-methoxyphenol (49.6 g, 349 mmol), 2,5-dibromo-4-fluorobenzoic acid (80 g, 269 mmol), ethyl acetate (1.316 mL, 13.43 mmol), cesium carbonate (192 g, 591 mmol) and toluene (1200 mL). To the mixture at was added copper(I) triflate toluene complex (2:1) (1.713 g, 8.06 mmol) and it was stirred at room temperature for 20 minutes. The solution was then heated to 75° C. for 16 hours at which point the toluene was removed under reduced pressure. The solution was dissolved in 1.5 liters of water and washed with 250 ml of EtOAc. The aqeuous layer was acidified to pH 1 with concentrated HCl and the resulting precipitant was collected by filtration and washed with water. The derived solid was washed with a 1:1 solution of ethyl acetate and hexane, then dried under vacuum to afford 5-bromo-4-fluoro-2-(2-fluoro-4-methoxyphenoxy)benzoic acid as a light brown solid. MS m/z=358.8 [M+H].

Aufarbeitung

  1. additionTo the mixture at was added copper(I) triflate toluene complex (2:1) (1.713 g, 8.06 mmol) and it
  2. customwas removed under reduced pressure
  3. dissolutionThe solution was dissolved in 1.5 liters of water
  4. washwashed with 250 ml of EtOAc
  5. filtrationthe resulting precipitant was collected by filtration
  6. washwashed with water
  7. washThe derived solid was washed with a 1:1 solution of ethyl acetate and hexane
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6d12180397b94f46aca8cdd87fa7b645
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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