Potassium Bromide → 3-(4'-Fluorobiphenyl-4-yl)propanal

HRID 84054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84054
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](O)=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br-].[K+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]=[O:17])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 1393679[1,1'-Biphenyl]-4-propanoicacid, 4'-fluoro-HCID 23665760Sodium Hypochlorite

Produkt 1

HCID 867009833-(4'-Fluorobiphenyl-4-yl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724126TempoKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of the compound obtained from step d above (0.7 g) in dichloromethane (10 mL), 2,2,6,6,-tetramethylpiperidine N-oxyl (4.74 mg) and potassium bromide (36.05 mg) were added at 0° C. under nitrogen atmosphere. Sodium hypochlorite (0.28 g, 4% solution) was added at pH 8-9 (maintained by adding aqueous sodium bicarbonate solution). The reaction mixture was stirred for 20 minutes at 0° C. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine. The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to afford the title compound (0.55 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2201077ade2a4358a4d05c745536fd23
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846910B2

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