Potassium Hydroxide → HCID 66611532, compound

HRID 1916431Notes

Reaction equation

HRID 1916431 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=O)[CH3:2].[OH-].[K+].Br[CH:20](C(OCC)=O)[C:21]([O:23]CC)=[O:22]>CCO.Cl.C(O)(=O)C>[CH3:2][C:1]1[C:4]2[C:5](=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=2)[C:6](=[O:7])[O:8][C:20]=1[C:21]([OH:23])=[O:22]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 69637Diethyl bromomalonateHCID 66611875HCID 66611875, compound

Product 1

HCID 66611532HCID 66611532, compoundYield 41.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1.12 g (4.8 mol) 2-acetyl-5-(trifluoromethyl)benzoic acid in EtOH (30 ml) were succesively added 270 mg (4.8 mmol) KOH and 1.15 g (4.8 mmol) diethyl 2-bromo-malonate at RT. The resulting mixture was heated at 90° C. for 6 h. After cooling to RT, the RS was concentrated in vacuo. The residue was taken up with water (30 ml) and extracted with EtOAc. The organic layer was washed with water (40 ml) and brine (30 ml), dried over Na2SO4 and concentrated in vacuo. This residue obtained was diluted with hydrochloric acid (10 ml) and acetic acid (6 ml) and the RS was heated at 90° C. for 2 h. After cooling to RT, the RS was poured into ice-water and the precipitate was filtered off to yield 540 mg (2.0 mmol, 41%) 4-methyl-1-oxo-7-(trifluoromethyl)-1H-isochromene-3-carboxylic acid, which was used in the next step without further purification.

Workup

  1. customat RT
  2. temperatureAfter cooling to RT
  3. concentrationthe RS was concentrated in vacuo
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water (40 ml) and brine (30 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThis residue obtained
  9. temperaturethe RS was heated at 90° C. for 2 h
  10. temperatureAfter cooling to RT
  11. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-eccc01a9b34a4601abb5cc77745a3efb
Source dataset
uspto-grants-2013_12
Patent number
US08618129B2

Reaction notes

Loading…