Bromine → HCID 2825186, compound

HRID 346096Notes

Reaction equation

HRID 346096 reaction equation
[CH:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)([CH3:3])[CH3:2].[Br:14]Br.S([O-])([O-])=O.[Na+].[Na+]>>[Br:14][C:6]12[CH2:12][CH:10]3[CH2:9][CH:8]([CH2:13][C:4]([CH:1]([CH3:3])[CH3:2])([CH2:11]3)[CH2:5]1)[CH2:7]2

Participants

4

Reactant 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 5244831-isopropyladamantane

Product 1

HCID 2825186HCID 2825186, compoundYield 83%

Procedure

Mix 0.034 mol of isopropyl adamantane (IV) with a ten times excess of bromine (0.33 mol). Heat slowly and stir under reflux for 4 h. Subsequently, allow to cool and pour onto ice water. Decompose the excess bromine with sodium sulfite until the aqueous solution has discolored. 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: 83%).

Workup

  1. temperatureHeat slowly
  2. temperatureunder reflux for 4 h
  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-e6f21f6a1ffb489a8c560faff0c039a8
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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