Water → 2-Allyloxy-2',6'-dichloro-5-fluorobiphenyl

HRID 902321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902321
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([OH:16])=[CH:11][CH:12]=[C:13]([F:15])[CH:14]=1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:19]([O:16][C:10]1[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=1[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[CH:18]=[CH2:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 691179112',6'-Dichloro-5-fluorobiphenyl-2-ol

Produkt 1

HCID 691175262-Allyloxy-2',6'-dichloro-5-fluorobiphenylAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2′,6′-dichloro-5-fluorobiphenyl-2-ol (11.63 g, 45 mmol) in DMF (150 mL) was added allyl bromide (5.8 mL, 67.5 mmol) and potassium carbonate (18.6 g, 135 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight and poured into water. The mixture was extracted with methylene chloride and washed with water. The solvent was removed under vacuum. Chromatography with 0–30% ethyl acetate in hexanes afforded 12.7 g (94%) of 2-allyloxy-2′,6′-dichloro-5-fluorobiphenyl as a light yellow oil. MS (EI) m/z 296 (M+).

Aufarbeitung

  1. extractionThe mixture was extracted with methylene chloride
  2. washwashed with water
  3. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3de75cc78a1440c1820744a854ff5763
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365095B2

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