Methyl 2-bromobenzoate → Methyl 2-(4-formylphenyl)benzoate

HRID 1594187

Reaktionsgleichung

Reaktionsgleichung von HRID 1594187
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1)=[O:2].[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1Br.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 11894Methyl 2-bromobenzoateHCID 62657Potassium Phosphate, TribasicHCID 21940015p-Formylphenylboric acid

Produkt 1

HCID 4325150Methyl 2-(4-formylphenyl)benzoateAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 4-formylphenylboric acid (6.7 g) in N,N-dimethylformamide (100 ml) were added 2-bromobenzoic acid methyl ester (6.5 g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0 g) and tripotassium phosphate (23 g). The reaction mixture was stirred for 5 hours at 75° C. The reaction mixture was filtrated and concentrated. To the residue were added 1N hydrochloric acid and ethyl acetate, and the mixture was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1) to give the title compound (4.1 g) having the following physical data.

Aufarbeitung

  1. filtrationThe reaction mixture was filtrated
  2. concentrationconcentrated
  3. additionTo the residue were added 1N hydrochloric acid and ethyl acetate
  4. concentrationthe mixture was concentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-06d6b051a5e24121b349c0301dee4eec
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300917B2

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