Boron tribromide → (4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol

HRID 1634377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634377
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:27][CH2:28][O:29]C)/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)[CH2:27][CH2:28][OH:29])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 25134Boron tribromideHCID 120566491-[(2E)-4-(4-Chlorophenyl)-2,3-difluoro-6-methoxy-2-hexenyl]-3-phenoxybenzene

Produkt 1

HCID 59032878(4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-olAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-methoxy-2-hexenyl]-3-phenoxybenzene (0.081 g, 0.189 mmol) in methylene chloride at −5° C. under nitrogen was added dropwise boron tribromide (0.5 ml of a 1 M solution in methylene chloride, 0.5 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight at room temperature. The reaction mixture was cooled to −5° C., diluted with methanol (10 ml) and concentrated in vacua. The residue was taken up in methanol (10 ml) and the solution again concentrated. The residue was taken up in methylene chloride (25 ml), washed successively with water, saturated aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated in vacuo to a brown gum. Chromatography of this gum on silica gel afforded the title compound as a tan syrup (0.057 g) which was characterized by 1HNMR, 19FNMR and mass spectral analysis.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to −5° C.
  2. concentrationconcentrated in vacua
  3. concentrationthe solution again concentrated
  4. washwashed successively with water, saturated aqueous sodium bicarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to a brown gum

Quellen und Nachweise

ORD-Eintrag
ord-af3eb2f1531d4e9090bee3447cce8b4b
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506800B2

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