Iodine → Cycloheptanol, 1-phenyl-

HRID 2192294Notes

Reaction equation

HRID 2192294 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[Cl-].[NH4+]>O1CCCC1>[C:5]1([C:11]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 807IodineHCID 7961BromobenzeneHCID 10400CycloheptanoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 16385Cycloheptanol, 1-phenyl-Yield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To magnesium (1.2 g) in anhydrous tetrahydrofuran (60 mL) under an environment of nitrogen was added a crystal of iodine followed by bromobenzene (7.85 g) at such a rate that the reaction maintained a steady reflux. The reaction mixture was stirred for 20 minutes then cycloheptanone (4.48 g) was added with care. After stirring for 10 minutes saturated aqueous ammonium chloride (10 mL) was added and the reaction was partitioned to between water (100 mL) and isohexane (100 mL). The organic layer was dried (MgSO4) and evaporated to afford the sub-titled compound (7.6 g) as an oil.

Workup

  1. temperaturemaintained a steady reflux
  2. additionwas added
  3. customthe reaction was partitioned to between water (100 mL) and isohexane (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7c8e6f1eafa84ffba088e5d3568e1763
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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