Water → HCID 71090169, compound

HRID 716819Notes

Reaction equation

HRID 716819 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.O>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:12])[C:10]2[CH:9]=[C:8]([O:11][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 9590p-Fluoronitrobenzene2×HCID 11430Potassium CarbonateHCID 57076460HCID 57076460, compound2×

Product 1

HCID 71090169HCID 71090169, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

3,3-Dimethyl-1,3-dihydro-2-benzofuran-5-ol (Intermediate 18, 500 mg, 3.04 mmol) and potassium carbonate (1.05 g, 7.6 mmol) were suspended in acetonitrile (7.5 mL). 1-Fluoro-4-nitrobenzene (386 mg, 2.74 mmol) was added and the mixture was stirred under nitrogen at 70° C. overnight and then for 4 hours at 80° C. Further 1-fluoro-4-nitrobenzene (86 mg, 0.6 mmol) was added and the mixture heated to reflux until achieving reaction completion. After cooling water and ethyl acetate were added and the two layers were separated. The organic phase was washed three times with brine, then it was dried over anhydrous Na2SO4 and concentrated to dryness. The residue was triturated in isopropanol and the solid washed with further isopropanol to give the title compound (500 mg).

Workup

  1. waitfor 4 hours at 80° C
  2. temperaturethe mixture heated
  3. temperatureto reflux
  4. customreaction completion
  5. additionwere added
  6. customthe two layers were separated
  7. washThe organic phase was washed three times with brine
  8. dry with materialit was dried over anhydrous Na2SO4
  9. concentrationconcentrated to dryness
  10. customThe residue was triturated in isopropanol
  11. washthe solid washed with further isopropanol

Sources & evidence

ORD record
ord-2be249746dd14c1b8e2d577d38f9bddf
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

Loading…