Acetic Acid → HCID 69234598, compound
Reaction equation
[Br-:1].[CH2:2]([N+:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:17]([O-])(=O)[CH3:18].[NH4+].[C:22]1(C)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.[C:30](O)(=O)[CH3:31]>>[Br:1][C:8]1[CH:7]=[CH:6][C:5]([C:3]2[C:2]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:11][C:16]([C:15]3[CH:14]=[CH:13][CH:12]=[CH:18][CH:17]=3)=[CH:30][CH:31]=2)=[CH:10][CH:9]=1Participants
Procedure
The synthetic intermediate (enone) 9.0 g 31 mmol), 1-phenacylpyridinium bromide 8.7 g (31 mmol) and ammonium acetate 19.3 g (25 mmol) were suspended in 27 ml of acetic acid and refluxed for 12 hours by heating. The reaction solution was cooled down to room temperature, and toluene and water were added thereto to separate the solution into two layers. Then, the organic layer was washed in order with a 10% sodium hydroxide aqueous solution and a saturated saline solution and dried on anhydrous sodium sulfate. After removing the organic solvent by distillation under reduced pressure, 27 ml of ethanol was added thereto, and deposited crystal was filtered and washed with ethanol to obtain 10.6 g (yield: 88%) of 4-bromophenyl-2,6-diphenylpyridine.
Workup
- temperaturerefluxed for 12 hours
- temperatureby heating
- customto separate the solution into two layers
- washThen, the organic layer was washed in order with a 10% sodium hydroxide aqueous solution
- dry with materiala saturated saline solution and dried on anhydrous sodium sulfate
- customAfter removing the organic solvent
- distillationby distillation under reduced pressure, 27 ml of ethanol
- additionwas added
- filtrationwas filtered
- washwashed with ethanol
Sources & evidence
- ORD record
- ord-4da5c3006e9847cc8aa424e4ad337873
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217570B2
Reaction notes
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