Lithium hydroxide, monohydrate → 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid

HRID 1187140Notes

Reaction equation

HRID 1187140 reaction equation
[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([O:14]C)=[O:13])[O:7][CH2:6][CH2:5]2.O[Li].O>CO.C1COCC1.O>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([OH:14])=[O:13])[O:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67516849methyl 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate

Product 1

HCID 666463356-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate (650 mg, 2.06 mmol) in 20 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (347 mg, 8.25 mmol), and the mixture was stirred at ambient temperature overnight. The solvents were removed under vacuum, and the residue was added 50 mL of water and extracted with ether. 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 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 50 mL of water
  3. extractionextracted with ether
  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-ca870f29e25b4bec9798cbab4e724775
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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