Sodium Iodide → (3-Iodopropyl)cyclopentane

HRID 397716Notes

Reaction equation

HRID 397716 reaction equation
BrC1C=CC(S(O[CH2:12][CH2:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=O)=O)=CC=1.[I-:20].[Na+]>CC(C)=O>[CH:15]1([CH2:14][CH2:13][CH2:12][I:20])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 230009943-Cyclopentylpropyl 4-bromobenzenesulfonate

Product 1

HCID 15508337(3-Iodopropyl)cyclopentaneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-cyclopentylpropyl 4-bromobenzenesulfonate (Preparation 12, 1.0 g, 2.85 mmol) in acetone (30 ml) was added sodium iodide (1.0 g, 6.67 mmol) and the reaction mixture was left to stir at room temperature for 16 h. The resulting precipitate was filtered and the filtrate was diluted with water (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a light pink oil (0.60 g, 90%).

Workup

  1. waitthe reaction mixture was left
  2. filtrationThe resulting precipitate was filtered
  3. additionthe filtrate was diluted with water (100 ml)
  4. extractionextracted with dichloromethane (100 ml)
  5. washThe extract was washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4a4b46a21084b6fbd2895328fa0a516
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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