Sodium Hydroxide → 5-Bromo-3-methyl-1-benzofuran

HRID 1403488Notes

Reaction equation

HRID 1403488 reaction equation
[C:1]([C:4]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].CC([O-])=O.[Na+].[OH-].[Na+]>C(OC(=O)C)(=O)C>[Br:15][C:13]1[CH:12]=[CH:11][C:5]2[O:6][CH:7]=[C:1]([CH3:2])[C:4]=2[CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 192613632-(2-Acetyl-4-bromophenoxy)acetic acid

Product 1

HCID 123375005-Bromo-3-methyl-1-benzofuranYield 93%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 2-(2-acetyl-4-bromophenoxy)acetic acid (5.3 g, 19.41 mmol) in acetic anhydride (100 mL) was added NaOAc (3.19 g, 38.90 mmol). The resulting solution was heated to reflux overnight. The pH value of the resulting solution was adjusted to 7 with aqueous sodium hydroxide, extracted with ether (50 mL×3), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by silica gel chromatography (petroleum ether) to afford 5-bromo-3-methyl-1-benzofuran as a light yellow oil (3.8 g, 93%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ether (50 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by silica gel chromatography (petroleum ether)

Sources & evidence

ORD record
ord-0164260e107c431c9c80f14973ae0938
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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