1-Methylimidazole → Bromodecyl(methylimidazolium)hydrobromide
Reaction equation
[Br:1][CH:2]([Br:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CC(C)=O>[BrH:1].[Br:12][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:15]1[NH:16][CH:17]=[CH:18][N+:14]=1[CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
A dry 250 mL Schlenk flask was equipped with a magnetic stir bar, dropping funnel, and sealed with a rubber septum. Dibromodecane (73.0 g, 0.24 mol) was dissolved in acetone (50 ml) and added to the flask. The mixture was heated to 55° C. in an oil bath, and 1-methylimidazole (4.0 g, 48.7 mmol) was added over 90 minutes via dropping funnel through the top of the flask under nitrogen flow. After addition, the reaction was allowed to stir at 55° C. for 6 hours. The reaction was cooled and solvent was removed in vacuo. The residue was diluted with 150 mL of hexanes and 60 mL of ethyl acetate and placed in a separatory funnel. The bottom layer was removed and purified by column chromatography over silica (dichloromethane/methanol, 9:1 v/v). Yield: 68%.
Workup
- customA dry 250 mL Schlenk flask was equipped with a magnetic stir bar
- customsealed with a rubber septum
- additionadded to the flask
- additionAfter addition
- temperatureThe reaction was cooled
- customsolvent was removed in vacuo
- additionThe residue was diluted with 150 mL of hexanes and 60 mL of ethyl acetate
- customplaced in a separatory funnel
- customThe bottom layer was removed
- custompurified by column chromatography over silica (dichloromethane/methanol, 9:1 v/v)
Sources & evidence
- ORD record
- ord-4f1ff46efd1f447ebac12335f02bb8cb
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181364B2
Reaction notes
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