Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl formate | HCID 7865 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 67246817 | HCID 67246817 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67245879 | HCID 67245879 | 55% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07964724B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-db9d6a9466414986b0a14cf324188c16 |
|---|
| Source note | uspto-grants-2011_06 |
|---|