Methanol → Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate

HRID 750116Notes

Reaction equation

HRID 750116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])[O:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O.[CH3:27]O>>[CH3:27][O:14][C:13]([C:6]1[O:7][C:8]([C:10]2[C:4]([C:5]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:3][C:2]([Br:1])=[CH:12][CH:11]=2)=[O:9])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 230607776-Bromo-4-phenyl-3-isocoumarincarboxylic acid

Product 1

HCID 66990710Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate

Procedure

To a solution of 6-bromo-4-phenylisocoumarin-3-carboxylic acid (10 g) in methanol (200 ml) was added sulfuric acid (20 ml) and the mixture was refluxed for 2 hrs. The reaction mixture was concentrated, and the residue was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was crystallized from isopropyl ether to give the title compound (9.76 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 2 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-4c4870a03c324597852f41505de2cb1b
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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