Acetone → 1-(2-Iodoethyl)adamantane

HRID 397728Notes

Reaction equation

HRID 397728 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 28, 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-9a9e04667aed48b78fffac061ba06671
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

Loading…