Iodine → 2-(4-Fluorophenyl)bicyclo[2.2.1]heptan-2-ol

HRID 1091993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091993
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].II.[CH2:12]1[CH:16]2[CH2:17][C:18](=[O:19])[CH:14]([CH2:15]2)[CH2:13]1>C1COCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2([OH:19])[CH2:17][CH:16]3[CH2:15][CH:14]2[CH2:13][CH2:12]3)=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 5462224Magnesium

Produkt 1

HCID 222978332-(4-Fluorophenyl)bicyclo[2.2.1]heptan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 1-bromo-4-fluorobenzene (5.00 ml, 45.5 mmol), magnesium turnings (3.32 g, 137 mmol), and a few iodine crystals in 70 ml dry THF were vigorously stirred for 4 hours under the protection of nitrogen and cooling with ice/water. Norcamphor (5.00 g, 45.5 mmol) dissolved in 10 ml dry THF was added drop-wise, and the reaction was allowed to warm up to room temperature and stirred overnight. The reaction was carefully quenched with water and decanted from the excess magnesium turnings. The reaction mixture in THF and water was adjusted to pH 7 with 2N HCl solution and extracted with chloroform (3×50 ml). The extract was dried over anhydrous sodium sulfate and the solvent was removed by vacuum evaporator. This resulted in an alcohol intermediate (III) appearing as a faintly yellow oil (9.4 g, 99%).

Aufarbeitung

  1. additionwas added drop-wise
  2. customThe reaction was carefully quenched with water
  3. customdecanted from the excess magnesium turnings
  4. extractionextracted with chloroform (3×50 ml)
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by vacuum evaporator

Quellen und Nachweise

ORD-Eintrag
ord-d9eba007f5e341d5abf57b6d84f5ca2a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129414B2

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