2-Acetylbenzofuran → 1-(1-Benzofuran-2-Yl)-2-Bromoethan-1-One

HRID 2269705Notes

Reaction equation

HRID 2269705 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[C:10]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH:17]=1)(=[O:12])[CH3:11]>C1COCC1>[Br:7][CH2:11][C:10]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH:17]=1)=[O:12]

Participants

3

Reactant 1

HCID 154352-Acetylbenzofuran

Product 1

HCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-OneYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridinium bromide perbromide (20 g) was added to a THF solution (200 ml) of 2-acetylbenzofuran (8.35 g). The reaction mixture was stirred at room temperature for 20 minutes. The precipitated crystals were collected by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the entitled compound (6.5 g).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c97de417ef544251ba3be6a4b3c31c26
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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