Bromine → 1-Bromo-3,5-dimethyl-7-ethyl Adamantane

HRID 346104Notes

Reaction equation

HRID 346104 reaction equation
[CH3:1][C:2]12[CH2:11][C:6]3([CH2:12][CH3:13])[CH2:7][CH:8]([CH2:10][C:4]([CH3:14])([CH2:5]3)[CH2:3]1)[CH2:9]2.[Br:15]Br.S([O-])([O-])=O.[Na+].[Na+]>>[Br:15][C:8]12[CH2:10][C:4]3([CH3:14])[CH2:5][C:6]([CH2:12][CH3:13])([CH2:11][C:2]([CH3:1])([CH2:3]3)[CH2:9]1)[CH2:7]2

Participants

4

Reactant 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 5193311,3-Dimethyl-5-ethyladamantane

Product 1

HCID 125617961-Bromo-3,5-dimethyl-7-ethyl AdamantaneYield 86%

Procedure

Mix 0.4 mol of 1,3-dimethyl-5-ethyl adamantane (III) with a ten times excess of bromine (4 mol). Heat slowly and stir for 4 hrs under reflux. Subsequently allow to cool and pour onto ice water. Decompose the excess bromine with sodium sulfite until discolouration of the aqueous solution. Then 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: 86%).

Workup

  1. temperatureHeat slowly
  2. temperatureunder reflux
  3. temperatureto cool
  4. additionpour onto ice water
  5. extractionThen 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-5fe2e6bad5484b5c9dfb781673be253f
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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