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

HRID 1007756Notes

Reaction equation

HRID 1007756 reaction equation
[CH3:1][C:2]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)=[O:3].[Br:13]Br>CCOCC.C(=O)([O-])O.[Na+]>[Br:13][CH2:1][C:2]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)=[O:3]

Participants

5

Reactant 2

HCID 154352-AcetylbenzofuranHCID 24408Bromine

Product 1

HCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-OneYield 69.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Benzofuran-2-yl methyl ketone (1.60 g, 10 mM) was dissolved in ether (20 mL). Under stirring of the mixture at room temperature, bromine (1.60 g) was added thereto. The resultant mixture was stirred for 10 minutes at room temperature, and poured in saturated sodium hydrogencarbonate solution, followed by extraction with ether (80 mL). The extract was washed with saturated brine and dried over magnesium sulfate, and the solvent was removed. Hexane was added to the residue and crystals were collected through filtration. The crystals were washed with hexane and dried, whereby 1.55 g of the product of interest was obtained (yield 69.4%).

Workup

  1. extractionfollowed by extraction with ether (80 mL)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed
  5. additionHexane was added to the residue and crystals
  6. filtrationwere collected through filtration
  7. washThe crystals were washed with hexane
  8. customdried

Sources & evidence

ORD record
ord-e8f54083fdfc427a94ecba332f93bd5c
Source dataset
uspto-grants-2004_09
Patent number
US06797711B2

Reaction notes

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