3,4-dihydro-2H-pyran → 2-(4-bromo-3-fluorophenoxy)tetrahydro-2H-pyran

HRID 84240

Reaktionsgleichung

Reaktionsgleichung von HRID 84240
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[F:26].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.CCOC(C)=O>ClCCl.CCCCCCC>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)=[CH:21][C:20]=1[F:26]

Komponenten

7

Edukt 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 27791534-Bromo-3-fluorophenolHCID 22033616Pyridinium.p-toluenesulfonate

Produkt 1

HCID 587212402-(4-bromo-3-fluorophenoxy)tetrahydro-2H-pyranAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

Pyridinium p-toluene sulfonic acid (789 mg, 3.1 mmol) was added to a solution of 4-bromo-3-fluorophenol (4.00 g, 20.9 mmol) and 3,4-dihydro-2H-pyran (3.52 g, 41.9 mmol) in dichloromethane (105 mL, 0.2M). After 2h the reaction was quenched with saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was extracted with dichloromethane (2×). The organic layers were combined, dried (Na2SO4), filtered and concentrated to give a colorless oil. The material was loaded onto a 25g silica guard column and run on a 330g column with 0-5% EtOAc in heptane. Desired material was concentrated down yielding 1900 mg (33%) of a clear colorless oil.

Aufarbeitung

  1. customAfter 2h the reaction was quenched with saturated aqueous sodium bicarbonate
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. concentrationDesired material was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-83d120aea195445e9ecc505c8ba48087
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846933B2

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