Sodium Acetate → 5-Bromobenzo[b]furan-3(2H)-one

HRID 1948681Notes

Reaction equation

HRID 1948681 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([C:8](=[O:11])[CH2:9]Cl)[CH:7]=1.C([O-])(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:12][CH2:9][C:8](=[O:11])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 137781301-(5-Bromo-2-hydroxyphenyl)-2-chloroethanone

Product 1

HCID 105127485-Bromobenzo[b]furan-3(2H)-oneYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.34 g (33.4 mmol) of 1-(5-bromo-2-hydroxyphenyl)-2-chloroethanone and 3.3 g (40.1 mmol) of anhydrous sodium acetate in 350 ml of methanol is heated at 65° C. for one hour, subsequently evaporated to dryness, the residue is taken up in 50 ml of water, and the aqueous mixture is extracted twice with 50 ml of methylene chloride each time. After the combined organic phases have been dried over sodium sulfate and the solvent has been stripped off, the crude product is purified by column chromatography on silica gel (n-heptane/methylene chloride 7:3), giving 2.14 g of 5-bromobenzofuran-3-one as yellow solid; LC/MS: 214 (M+H).

Workup

  1. customsubsequently evaporated to dryness
  2. extractionthe aqueous mixture is extracted twice with 50 ml of methylene chloride each time
  3. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  4. customthe crude product is purified by column chromatography on silica gel (n-heptane/methylene chloride 7:3)

Sources & evidence

ORD record
ord-9be64a272b8f4611b88af1a2e2404b23
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Reaction notes

Loading…