Potassium Carbonate → 3-Chloro-biphenyl-4-carboxaldehyde

HRID 631022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631022
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([Cl:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCCC.C(Cl)(Cl)Cl>O1CCCC1.O.[Cl-].[Na+].O.[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>[Cl:10][C:4]1[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 141091094-Bromo-2-chlorobenzaldehydeHCID 21875152Heptane chloroforme

Produkt 1

HCID 214412843-Chloro-biphenyl-4-carboxaldehydeAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5 g (22.78 mmol) of 4-bromo-2-chlorobenzaldehyde in 30 ml of tetrahydrofurane are successively added 3.47 g (28.47 mmol) of phenylboronic acid, 4.72 g (34.17 mmol) of potassium carbonate dissolved in 15 ml of water and 263 mg (0.01 equivalent) of tetrakis(triphenylphosphine) palladium. The reaction mixture is heated at 80° C. for 3 hrs. The reaction mixture is then cooled to ambient temperature and poured on 150 ml of brine. The watery layer is extracted three times with dichloromethane and the combined organic layers are successively washed by a 1M solution of sodium hydroxide, brine and filtered over a ChemElut cartridge to yield after concentration 4.6 g of a brown solid. Column chromatography (gradient heptane/chloroforme) yielded 3.29 g (65% yield) of 3-chlorobiphenyl-4-carbaldehyde as a white solid; mp=90-91° C.

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to ambient temperature
  2. extractionThe watery layer is extracted three times with dichloromethane
  3. washthe combined organic layers are successively washed by a 1M solution of sodium hydroxide, brine
  4. filtrationfiltered over a ChemElut cartridge
  5. customto yield after concentration 4.6 g of a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-14c618b243394265b0c2ce4dd9eb748c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320277B2

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