Acetone → 1-(2-Iodoethyl)adamantane

HRID 428966Notes

Reaction equation

HRID 428966 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 filtratc was diluted with water (100 ml) and extracted with dichlioromethane (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 filtratc was diluted with water (100 ml)
  4. extractionextracted with dichlioromethane (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-f8455b8ea5884107be856c53b34d30c5
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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