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

HRID 2087093Notes

Reaction equation

HRID 2087093 reaction equation
[BrH:1].N1C=CC=CC=1.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9]1[C:17]([CH3:19])=[O:18]>CO>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[C:9]1[C:17](=[O:18])[CH2:19][Br:1]

Participants

4

Reactant 2

HCID 154352-AcetylbenzofuranHCID 87810Pyridine, hydrobromide (1:1)

Product 1

HCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-OneYield 120.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A polymer of perbromide of pyridine hydrobromide (8.75 g; 17.5 mmol; 1.4 equivalent) is added to a solution of (benzofuran-2-yl)methylketone (2 g; 12.5 mmol) in methanol (40 ml). The resulting mixture is stirred at ambient temperature for 7 hours and the reaction is stopped by filtration. The methanol is eliminated under reduced pressure and an additional addition of diethyl ether allows crystallization of the expected product (3.6 g; yield=60%).

Workup

  1. filtrationthe reaction is stopped by filtration
  2. additionan additional addition of diethyl ether

Sources & evidence

ORD record
ord-8b062b5ecece4b5c84180c77d59ef961
Source dataset
uspto-grants-2004_04
Patent number
US06727269B1

Reaction notes

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