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

HRID 2368756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368756
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-c8b90d6f30ee4db8823e25314d0fb032
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703799B2

Notizen zur Reaktion

Wird geladen…