Sodium Carbonate → Methyl 3-bromo-5-(4-fluorophenyl)benzoate

HRID 1726384

Reaktionsgleichung

Reaktionsgleichung von HRID 1726384
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOCCOC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 621923Methyl 3,5-Dibromobenzoate

Produkt 2

HCID 69062042Methyl 3,5-di(4-fluorophenyl)benzoateAusbeute 4 %HCID 69068418Methyl 3-bromo-5-(4-fluorophenyl)benzoateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
88 °C

Versuchsvorschrift

To a solution of methyl 3,5-dibromobenzoate (3.00 g, 10.2 mmol) and 4-fluoro-phenyl boronic acid (1.43 g, 10.2 mmol) in 2-methoxyethyl ether (60 ml) and ethanol (3 ml) was added Na2CO3 (saturated, 9 ml), followed by tetrakis(triphenylphosphine) palladium (0) (0.2 g). The mixture was heated at 88° C. for 1.5 h, then cooled to room temperature, partitioned between hexane and water, and the organic phase washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to yield methyl 3-bromo-5-(4-fluorophenyl)benzoate (intermediate XXXIVa, 0.725 g, 23%) as a white solid, and methyl 3,5-di(4-fluorophenyl)benzoate (intermediate XXXIVb, 0.128 g, 4%) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between hexane and water
  3. washthe organic phase washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationthe organic solution concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f7d2824e37d748efbaa5e49b5eac6485
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491821B2

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