Ethanol → 7-(4-Fluorophenyl)-1-tetralone

HRID 1277028Notes

Reaction equation

HRID 1277028 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25](O)[CH3:26]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:21]2[CH:22]=[C:23]3[C:18]([CH2:24][CH2:25][CH2:26][C:12]3=[O:15])=[CH:19][CH:20]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 867561584-Fluorophenyl borate

Product 1

HCID 184723477-(4-Fluorophenyl)-1-tetralone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Under argon atmosphere, a mixture of 7-(trifluoromethanesulfoxy)-1-tetralone (17.5 g), 4-fluorophenyl borate (10.0 g), potassium carbonate (16.6 g), toluene (500 ml), ethanol (50 ml) and water (50 ml) was stirred at room temperature for 30 minutes, and to the mixture was added tetrakis(triphenylphosphine)palladium (2.08 g). The mixture was refluxed for 14 hours. The reaction mixture was cooled to room temperature. The organic layer was separated, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene=1/10) to give 7-(4-fluorophenyl)-1-tetralone (13.8 g) as brown oil.

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate/toluene=1/10)

Sources & evidence

ORD record
ord-4fd3409745e64b7989d29876974ea564
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

Loading…