Acetone → HCID 22176354, compound

HRID 1797497Notes

Reaction equation

HRID 1797497 reaction equation
[C:1]([C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:26](C(OCC)=O)[C:27]([O:29]CC)=[O:28].CC(C)=O>CN(C)C=O>[Br:18][C:16]1[CH:17]=[C:9]2[C:10](=[CH:14][CH:15]=1)[CH2:11][O:13][C:26]([C:27]([OH:29])=[O:28])=[C:1]2[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 3467342-Benzoyl-4-bromobenzoic acid

Product 1

HCID 22176354HCID 22176354, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzoyl-4-bromobenzoic acid (25 g, 82 mmol), potassium carbonate (12 g, 87 mmol), diethyl bromomalonate (22 g, 92 mmol), acetone (450 mL) and N,N-dimethylformamide (8 mL) was stirred at room temperature for 15 h. The solvent was evaporated under reduced pressure. The residue was poured into water and extracted with ethyl acetate. The residue was crystallized from hexane and the crystals were collected by filtration. The obtained crystals were added to a mixture of acetic acid (235 mL) and concentrated hydrochloric acid (360 mL) and the mixture was stirred at 120° C. for 8 h. The reaction mixture was cooled and concentrated. The residue was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration, washed with diisopropyl ether and dried to give 6-bromo-4-phenyl-1H-isochromene-3-carboxylic acid (17 g, 60%) as crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. customThe residue was crystallized from hexane
  5. filtrationthe crystals were collected by filtration
  6. additionThe obtained crystals were added to a mixture of acetic acid (235 mL) and concentrated hydrochloric acid (360 mL)
  7. stirringthe mixture was stirred at 120° C. for 8 h
  8. temperatureThe reaction mixture was cooled
  9. concentrationconcentrated
  10. additionThe residue was poured into water
  11. extractionextracted with ethyl acetate
  12. washThe extract was washed with brine
  13. dry with materialdried with anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. filtrationThe precipitated crystals were collected by filtration
  16. washwashed with diisopropyl ether
  17. customdried

Sources & evidence

ORD record
ord-2d622e3a1ab44b98b26c8abb3d70dc69
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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