Sodium Iodide → (3-Iodopropyl)cyclopentane
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- waitthe reaction mixture was left
- filtrationThe resulting precipitate was filtered
- additionthe filtrate was diluted with water (100 ml)
- extractionextracted with dichloromethane (100 ml)
- washThe extract was washed with brine (100 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a4a4b46a21084b6fbd2895328fa0a516
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610711B2
Reaction notes
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