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

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

Reactant 3

HCID 24408Bromine2×

HCID 24437Sodium Sulfite

HCID 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%).