Acetone → 1-(2-Iodoethyl)adamantane

HRID 1826478Notes

Reaction equation

HRID 1826478 reaction equation
BrC1C=CC(S(OCC[CH:14]2[CH:21]3[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)(=O)=O)=CC=1.[I-:24].[Na+].C[C:27]([CH3:29])=O>>[C:19]12([CH2:29][CH2:27][I:24])[CH2:18][CH:17]3[CH2:22][CH:21]([CH2:14][CH:15]([CH2:16]3)[CH2:23]1)[CH2:20]2

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 544780962-Adamantylethyl 4-bromobenzenesulfonate

Product 1

HCID 221412941-(2-Iodoethyl)adamantaneYield 75%

Procedure

To a solution of 2-adamantylethyl 4-bromobenzenesulfonate (Preparation 92, 1.0 g, 2.5 mmol) in acetone (25 ml) was added sodium iodide (0.75 g, 5 mmol) and the reaction mixture was left to stir at room temperature for 72 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 white crystalline solid (0.54 g, 75%).

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-698718f7f66043e188a0356b4f5bdea6
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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