Sodium Carbonate → Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoate

HRID 1460364

Reaktionsgleichung

Reaktionsgleichung von HRID 1460364
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[CH3:11].Br[C:13]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>O.C(O)C.C1(C)C=CC=CC=1>[CH3:11][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])[CH:6]=[CH:7][C:2]=1[F:1]

Komponenten

8

Edukt 4

HCID 10340Sodium Carbonate2×HCID 14923Ammonium HydroxideHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 2774580(4-Fluoro-3-methylphenyl)boronic acid

Produkt 1

HCID 15037296Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoateAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-fluoro-3-methylphenylboronic acid (6.5 g, 42.5 mmol), methyl 2-bromo-5-fluorobenzoate (10.0 g, 42.9 mmol), tetrakis (triphenylphospine) palladium(0) (1.0 g, 0.87 mmol, 0.2 eq), toluene (100 mL), 2M aqueous sodium carbonate (50 mL) and ethanol (25 mL) was refluxed for 9 h. The reaction mixture was then poured into 50 mL each of concentrated ammonium hydroxide, 2M aqueous sodium carbonate, and water, the organic phase was separated, and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, and concentrated to leave an oil which was chromatographed on silica gel using hexane to provide 11 g (98%) of the ester.

Aufarbeitung

  1. temperaturewas refluxed for 9 h
  2. customthe organic phase was separated
  3. extractionthe aqueous was extracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto leave an oil which
  8. customwas chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d58dfe5feaa74d62a802ffa05488e10c
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070100

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