Bromine → 1-Bromo-3-ethyladamantane

HRID 346105

Reaction equation

HRID 346105 reaction equation
[CH2:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2)[CH3:2].[Br:13]Br.S([O-])([O-])=O.[Na+].[Na+]>>[Br:13][C:5]12[CH2:11][CH:9]3[CH2:8][CH:7]([CH2:12][C:3]([CH2:1][CH3:2])([CH2:10]3)[CH2:4]1)[CH2:6]2

Participants

4

Reactant 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 5226371-Ethyladamantane

Product 1

HCID 27355671-Bromo-3-ethyladamantaneYield 83%

Procedure

Mix 0.034 mol of ethyl adamantane with a ten times excess of bromine (0.33 mol). Heat slowly and stir under reflux for 4 hrs. Then allow to cool and pour onto ice water. Decompose the excess bromine with sodium sulfite until discoloration of the aqueous solution. Subsequently extract with ether, wash the combined organic phases with sodium bicarbonate solution, dry with magnesium sulfate, filter and evaporate to dryness under vacuum. Recrystallize the residue from methanol. (Yield: 83%).

Workup

  1. temperatureHeat slowly
  2. temperatureunder reflux for 4 hrs
  3. temperatureto cool
  4. additionpour onto ice water
  5. extractionSubsequently extract with ether
  6. washwash the combined organic phases with sodium bicarbonate solution
  7. dry with materialdry with magnesium sulfate
  8. filtrationfilter
  9. customevaporate to dryness under vacuum
  10. customRecrystallize the residue from methanol

Sources & evidence

ORD record
ord-615d3b11111c44609f0f8bf0716b3eb3
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Linked notes

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