Ethyl 5-bromo-3-methyl-4-[(propan-2-yl)oxy]-1-benzofuran-2-carboxylate → 5-Bromo-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid

HRID 29474Notes

Reaction equation

HRID 29474 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=[O:11])=[C:7]([CH3:15])[C:6]=2[C:16]=1[O:17][CH:18]([CH3:20])[CH3:19]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([CH3:15])[C:6]=2[C:16]=1[O:17][CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 53428887Ethyl 5-bromo-3-methyl-4-[(propan-2-yl)oxy]-1-benzofuran-2-carboxylate

Product 1

HCID 687122265-Bromo-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acidYield 86.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.58 g (1.7 mmole) of ethyl 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylate in 15 mL of THF and 15 mL MeOH was added 8.5 mL of 1NaOH and the reaction was stirred at room temperature for 1 hour. The solvent was concentrated in vacuo, the residue was neutralized with 1N HCl and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to provide 0.46 g of 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylic acid. Yield 86.8%; m.p. 182-184° C.; MS 311.0 (M−H)−.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b1249423244d01bd5f917abd46ad78
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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