1-(1-Benzofuran-3-yl)ethan-1-one → 1-(Benzofuran-3-yl)-2-bromoethanone

HRID 362257

Reaction equation

HRID 362257 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.[C:34]([C:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[O:40][CH:41]=1)(=[O:36])[CH3:35]>O1CCCC1>[Br:1][CH2:35][C:34]([C:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[O:40][CH:41]=1)=[O:36]

Participants

4

Reactant 2

HCID 112866121-(1-Benzofuran-3-yl)ethan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 27765801-(Benzofuran-3-yl)-2-bromoethanoneYield 27.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenyltrimethylammonium tribromide (2.47 g) in tetrahydrofuran (20 ml) was added dropwise at ambient temperature under nitrogen over 5 minutes to a stirred solution of 3-acetylbenzo[b]furan (1 g) in tetrahydrofuran (20 ml), then the mixture was stirred at ambient temperature for a further 1.5 hours, filtered, and the solvent removed in vacuo. The residue was triturated with ether, and the resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 3-(2-bromoacetyl)benzo[b]furan as an off-white solid (0.25 g).

Workup

  1. filtrationfiltered
  2. customthe solvent removed in vacuo
  3. customThe residue was triturated with ether
  4. filtrationthe resulting solid was collected by filtration
  5. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-10b5b665c38b46309fa8f6f6837d9876
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Linked notes

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