Methyl Benzoate → (Trifluoromethyl)benzene

HRID 8425

Reaction equation

HRID 8425 reaction equation
[C:1]1(S(C(F)(F)F)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[K])(C)(C)C.C(OC)(=O)C1C=CC=CC=1.[F:30][C:31]([F:41])([F:40])C(C1C=CC=CC=1)=O.IC1C=CC=CC=1>[Cu](I)I>[F:30][C:31]([F:41])([F:40])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 7150Methyl BenzoateHCID 99052,2,2-TrifluoroacetophenoneHCID 11575IodobenzeneHCID 178419081HCID 178419081, compound2×

Product 1

HCID 7368(Trifluoromethyl)benzeneYield 26%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

The trifluoromethyl phenyl sulfone/tBuOK trifluoromethylation method can also be applied to other systems. For instance, methyl benzoate can be trifluoromethylated to generate 2,2,2-trifluoroacetophenone in 30% yield at about −50° C. to about −20° C. CF3Cu can be in situ generated with trifluoromethyl phenyl sulfone/tBuOK and copper iodide (CuI), and then further react with iodobenzene at 80° C. for 20 h to give α,α,α-trifluorotoluene in 26% yield.

Workup

  1. customat about −50° C. to about −20° C

Sources & evidence

ORD record
ord-a6ef70945a064cf8aa5b23fae875897f
Source dataset
uspto-grants-2006_08
Patent number
US07087789B2

Linked notes

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