Methyl formate → HCID 67245879, compound

HRID 2425589Notes

Reaction equation

HRID 2425589 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](I)=[C:7]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O-].[Na+].[CH3:21][O:22][CH:23]=[O:24]>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:23]([O:22][CH2:21][CH3:18])=[O:24])=[C:7]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 10942334Sodium MethoxideHCID 67246817HCID 67246817, compound

Product 1

HCID 67245879HCID 67245879, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a degassed solution of 4-tert-butyl-1-iodo-2-(2,2,2-trifluoro-ethoxy)benzene (2.5 g, 6.9 mmol), sodium methoxide (0.57 g, 10.4 mmol) and dichlorobistriphenylphosphinepalladium (0.25 g, 0.3 mmol) in dioxane (6 mL) was added methylformate (0.86 mL, 14.0 mmol). The resulting mixture was heated in an oil bath (60° C.) for 18 h and then allowed to cool. The solution was diluted with dioxane and filtered through a plug of Celite and concentrated. Purification of the crude residue by flash chromatography over silica gel using 5-15% ethyl acetate in hexane gave ethyl 4-tert-butyl-2-(2,2,2-trifluoroethoxy)benzoate (1.1 g, 55%) as a clear oil.

Workup

  1. temperatureto cool
  2. filtrationfiltered through a plug of Celite
  3. concentrationconcentrated
  4. customPurification of the crude residue by flash chromatography over silica gel using 5-15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-db9d6a9466414986b0a14cf324188c16
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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