Water → 2,3-Difluoro-4'-pentyl-1,1'-biphenyl

HRID 241477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241477
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.O>CC(C)=O>[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1450574-IodopentylbenzeneHCID 2734333(2,3-Difluorophenyl)boronic acid

Produkt 1

HCID 105874252,3-Difluoro-4'-pentyl-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1-Iodo-4-pentylbenzene (82 g, 0.3 mol), potassium carbonate (100 g, 0.72 mol), 2,3-difluorophenyl boronic acid (47 g, 0.3 mol), water (100 ml) and acetone (300 ml) were placed in a round-bottom three necked flask equipped with condenser, thermometer, mechanical stirrer, nitrogen inlet and outlet. The reaction flask was flushed with nitrogen and minor flow was held during whole reaction time. The mixture was heated up to the boiling point to degas the reaction system and then cooled down to 40° C. and the catalyst palladium acetate (0.1 g) was added. The temperature has increased by a few degrees and the solution turned brown. The mixture was refluxed for three days, then it was cooled down, poured on cold water and extracted with dichlorometane and the organic phase separated, dried over MgSO4 and dichlorometane was distilled off. The residue was distilled under reduced pressure at 0.2 mmHg collecting the fraction at 133° C. The colorless liquid fraction 41.5 g of was obtained, 53% of theor. yield.

Aufarbeitung

  1. customequipped with condenser
  2. customThe reaction flask was flushed with nitrogen and minor flow
  3. temperatureThe mixture was heated up to the boiling point
  4. customto degas the reaction system
  5. additionthe catalyst palladium acetate (0.1 g) was added
  6. temperatureThe temperature has increased by a few degrees
  7. temperatureThe mixture was refluxed for three days
  8. temperatureit was cooled down
  9. additionpoured on cold water
  10. extractionextracted with dichlorometane
  11. customthe organic phase separated
  12. dry with materialdried over MgSO4 and dichlorometane
  13. distillationwas distilled off
  14. distillationThe residue was distilled under reduced pressure at 0.2 mmHg
  15. customcollecting the fraction at 133° C
  16. customThe colorless liquid fraction 41.5 g of was obtained
  17. customyield

Quellen und Nachweise

ORD-Eintrag
ord-19d46c9fa7b74b4b8b1c3ace7ad2c083
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08652353B2

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