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

HRID 2368756Notes

Reaction equation

HRID 2368756 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c8b90d6f30ee4db8823e25314d0fb032
Source dataset
uspto-grants-2014_04
Patent number
US08703799B2

Reaction notes

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