Anisole → 4-Methoxy-2'-trifluoromethylbenzophenone

HRID 1857212Notes

Reaction equation

HRID 1857212 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[N+](C)([O-])=O>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:13]([C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]([F:9])([F:20])[F:21])=[O:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 2733225Ytterbium triflate

Product 1

HCID 221326914-Methoxy-2'-trifluoromethylbenzophenoneYield 50%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To commercially available nitromethane (10 ml) were added commercially available anisole (1.081 g), commercially available 2-(trifluoromethyl)benzoyl chloride (2.086 g) and commercially available ytterbium(III) trifluoromethanesulfonate (620 mg), and the admixture was stirred at 60° C. for 6 hours. The reaction mixture was partitioned between water and chloroform, abd the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate to obtain 1.402 g of the title compound (yield: 50%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform, abd the chloroform layer
  2. dry with materialwas then dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-20f372fe76ba4ade9b0743cf3de6bf38
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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