Ethyl Acetate → 2'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 1394158

Reaktionsgleichung

Reaktionsgleichung von HRID 1394158
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.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>[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[Cl:8])=[CH:13][CH:12]=1)=[O:10]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 127541-Bromo-2-chlorobenzeneHCID 5910734-Formylphenylboronic Acid

Produkt 1

HCID 13944002'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-bromochlorobenzene (0.24 mL, 2 mmol) and 4-formylbenzeneboronic acid (0.35 g, 2.2 mmol) in toluene (20 mL) were added 2M aq. sodium carbonate (2.6 mL) followed by (Ph3P)4Pd (0.34 g, 0.3 mmol). The resulting reaction mixture was refluxed for 3 h, cooled and diluted ethyl acetate. The organic phase was washed with water, saturated aq. sodium bicarbonate, brine and dried over sodium sulfate. The filtrate was concentrated in vacuo and the residue obtained was purified by chromatography (hexane:ethyl acetate; 4:1) to yield the title product.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 3 h
  3. temperaturecooled
  4. washThe organic phase was washed with water, saturated aq. sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue obtained
  8. customwas purified by chromatography (hexane:ethyl acetate; 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c73cff83589e435d93d15875f07dee8c
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348348B2

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