Phenyltrimethylammonium bromide dibromide → 1-[1-(Benzo[b]thiophen-2-yl)cyclobutyl]-2-bromoethanone
Reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[S:34]1[C:38]([C:39]2([C:43](=[O:45])[CH3:44])[CH2:42][CH2:41][CH2:40]2)=[CH:37][C:36]2[CH:46]=[CH:47][CH:48]=[CH:49][C:35]1=2>O1CCCC1>[S:34]1[C:38]([C:39]2([C:43](=[O:45])[CH2:44][Br:1])[CH2:40][CH2:41][CH2:42]2)=[CH:37][C:36]2[CH:46]=[CH:47][CH:48]=[CH:49][C:35]1=2Participants
4
Procedure
Phenyltrimethylammonium tribromide (1.72 g) was added in portions at −20° C. to a stirred solution of 1-[1-(benzo[b]thiophen-2-yl)cyclobutyl]ethanone (1.05 g) in tetrahydrofuran (50 ml). The mixture was stirred at ambient temperature for 3 hours, then it was filtered, and allowed to stand at ambient temperature for a further 18 hours. The mixture was filtered once more, and the solvent was removed in vacuo. The residue was purified via flash chromatography over silica using a 1:49 mixture of ether and petroleum ether (b.p. 40-60° C.) as eluant. Appropriate fractions were combined, and the solvents removed in vacuo to give 1-[1-(benzo[b]thiophen-2-yl)cyclobutyl]-2-bromoethanone as an oil (0.46 g).
Workup
- filtrationit was filtered
- waitto stand at ambient temperature for a further 18 hours
- filtrationThe mixture was filtered once more
- customthe solvent was removed in vacuo
- customThe residue was purified via flash chromatography over silica using
- additiona 1:49 mixture of ether and petroleum ether (b.p. 40-60° C.) as eluant
- customthe solvents removed in vacuo
Sources & evidence
- ORD record
- ord-b14f2092c43a4999bf7c84394d935ec0
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187802B1
Reaction notes
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