Iodide Ion → Methyl 4-methoxy-3-(trifluoromethyl)benzoate

HRID 1291704

Reaction equation

HRID 1291704 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[F:14][C:15]([F:20])([F:19])C([O-])=O.[K+].[I-].C([O-])(O)=O.[Na+]>CN(C=O)C.[Cu]>[F:14][C:15]([F:20])([F:19])[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 30165Iodide IonHCID 316980Methyl 3-iodo-4-methoxybenzoateHCID 516892Sodium BicarbonateHCID 23662811Potassium trifluoroacetate

Product 1

HCID 19360538Methyl 4-methoxy-3-(trifluoromethyl)benzoateYield 77.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

9.7 g of methyl 3-iodo-4-methoxybenzoate, 9.4 g of potassium trifluoroacetate and 12.9 g of copper(l) iodide were heated at 160° C. for 5 h in 250 ml of DMF. The mixture was poured onto 500 ml of NaHCO3 solution, the precipitate which was deposited was filtered off and both the precipitate and the aqueous phase were extracted with ethyl acetate. The combined organic phases were concentrated, and the residue was purified by flash chromatography using hexane/ethyl acetate 3:1. 6 g of methyl 3-trifluoromethyl-4-methoxybenzoate were obtained;

Workup

  1. filtrationthe precipitate which was deposited was filtered off
  2. extractionboth the precipitate and the aqueous phase were extracted with ethyl acetate
  3. concentrationThe combined organic phases were concentrated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ce3c3b4200cc498cb08ef71787a4633b
Source dataset
uspto-grants-1998_05
Patent number
US05753710

Linked notes

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