Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl 4-(bromomethyl)benzoate | HCID 954261 | — |
| Reactant | 3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol | HCID 57421231 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 46940553 | HCID 46940553 | 74.7% |
Reaction Steps
To a solution of 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenol (120 mg, 0.35 mmol) in acetone (3 ml) were added ethyl 4-(bromomethyl)benzoate (197 mg, 0.78 mmol), potassium iodide (9 mg, 0.05 mmol) and potassium carbonate (108 mg, 0.78 mmol). The mixture was stirred for 17 h at 60° C. The reaction mixture was concentrated. Water and EtOAc were added and the mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (20 g silica gel, heptane/EtOAc 9:1) to give title compound as colorless viscous oil (133 mg). MS (m/e, ISP neg. ion)=507.1 [M−H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08138189B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-fa3259b8983a4522a20a41a5b26cbc68 |
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| Source note | uspto-grants-2012_03 |
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