2-Acetylbenzo[b]thiophene → 1-(1-Benzothiophen-2-yl)-2-bromoethan-1-one

HRID 2183631Notes

Reaction equation

HRID 2183631 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](=[O:41])[CH3:40])=[CH:37][C:36]2[CH:42]=[CH:43][CH:44]=[CH:45][C:35]1=2>O1CCCC1>[S:34]1[C:38]([C:39](=[O:41])[CH2:40][Br:1])=[CH:37][C:36]2[CH:42]=[CH:43][CH:44]=[CH:45][C:35]1=2

Participants

4

Reactant 2

HCID 898052-Acetylbenzo[b]thiopheneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 27952581-(1-Benzothiophen-2-yl)-2-bromoethan-1-oneYield 193.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (32.04 g) was added in portions under nitrogen at 0° C. over 10 minutes to a stirred solution of 1-(benzo[b]thiophen-2-yl]ethan-1-one (15.0 g) in tetrahydrofuran (400 ml), the mixture was stirred at ambient temperature for 5 hours, then it was filtered and the solvent was removed in vacuo. The residue was triturated with a 9:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate (50 ml) and the resulting solid was collected by filtration and dried in vacuo to give 1-(benzo[b]thiophen-2-yl)-2-bromoethan-1-one (24.40 g) as a brown solid which was used without further purification.

Workup

  1. filtrationit was filtered
  2. customthe solvent was removed in vacuo
  3. customThe residue was triturated with a 9:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate (50 ml)
  4. filtrationthe resulting solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b2eb0085e4724f7c87de3f21f6027aa1
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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