Hydrochloric Acid → 1-(5-Bromo-7-Methoxy-1-Benzofuran-2-Yl)Ethan-1-One

HRID 53950

Reaction equation

HRID 53950 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21](=[O:23])[CH3:22].Cl>CN(C)C=O.C(OCC)(=O)C>[C:21]([C:22]1[O:10][C:5]2[C:4]([O:11][CH3:12])=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=1)(=[O:23])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 14913661-(5-Bromo-7-Methoxy-1-Benzofuran-2-Yl)Ethan-1-OneYield 34.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

10.0 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde was dissolved in 39 ml of N,N-dimethylformamide, and the resulting solution was mixed with 11.9 g of anhydrous potassium carbonate and stirred at room temperature. 5.0 g of chloroacetone was added dropwise to the above reaction solution at the same temperature, followed by additional 1 hour of stirring at an elevated temperature of 80° C. The resulting reaction solution was diluted with ethyl acetate and adjusted to pH 2 with concentrated hydrochloric acid, and the resulting organic layer was collected. The organic layer was dried to distill off the solvent, and the resulting residue was purified by silica gel column chromatography, thereby obtaining 4.0 g of 2-acetyl-5-bromo-7-methoxybenzofuran.

Workup

  1. stirringof stirring at an elevated temperature of 80° C
  2. customThe resulting reaction solution
  3. customthe resulting organic layer was collected
  4. customThe organic layer was dried
  5. distillationto distill off the solvent
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-def38f8df3a04e8f826ec714da64bd55
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Linked notes

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