Lithium hydroxide, monohydrate → 7-bromobenzofuran-3-carboxylic acid

HRID 2173291Notes

Reaction equation

HRID 2173291 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]([O:13]CC)=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O[Li].O>CO.C1COCC1.O>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]([OH:13])=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21694197HCID 21694197, compound

Product 1

HCID 656695287-bromobenzofuran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 7-bromo-1-benzofuran-3-carboxylate (1.0 g, 3.7 mmol) in 20 mL of MeOH/THF/H2O (2/211) was added LiOH H2O (777 mg, 18.5 mmol), and the mixture was stirred at ambient temperature overnight. The solvents were removed under vacuum, and the residue was added 10 mL of water and extracted with ether (100 mL). The aqueous layer was then acidified with 4 N HCl to pH=3 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 7-bromo-1-benzofuran-3-carboxylic acid.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 10 mL of water
  3. extractionextracted with ether (100 mL)
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c5eef8cc7c504d9ba82c9937127bdd2e
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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