Methanol → 2-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenol

HRID 916007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916007
[CH2:1]([C:8]([OH:26])([CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[O:24]C)([CH3:16])[CH3:15])[C:9]([F:12])([F:11])[F:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl.O>[CH2:1]([C:8]([OH:26])([C:9]([F:10])([F:12])[F:11])[CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[OH:24])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 102372232-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol

Produkt 1

HCID 589599242-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenolAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 49 mg (0.13 mmol) of 2-benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (Example 4) in 0.5 mL of dichloromethane, 1 mL (1.0 mmol) of 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at room temperature for 3 hours and was then cautiously added to cold MeOH and stirred for 20 minutes. The mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was chromatographed on silica gel using first hexanes then EtOAc-hexanes (0.5:99.5 to 1:99) to afford 31 mg (65%) of the title compound as a clear oil.

Aufarbeitung

  1. stirringstirred for 20 minutes
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed on silica gel using first hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dda5af2e852a4b80819f0ced98d3bb46
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268152B2

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