Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(Bromomethyl)-4-(trifluoromethyl)benzene | HCID 123062 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66701165 | HCID 66701165 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66701230 | HCID 66701230 | 70.8% |
Reaction Steps
To 0.190 g of 4-fluoro-1-hydroxynaphthalene-2-carboxylic acid methyl ester in 4 ml of dry DMF 560 mg of Cesium carbonate and 31 mg of potassium iodide was added. The mixture was stirred at ambient temperature for 20 minutes after which was added a solution of 0.31 g of 4-(trifluoromethyl)benzyl bromide in 2 ml of DMF. The mixture was stirred at room temperature for 3 h, poured into saturated sodium bicarbonate, extracted with ethyl acetate, washed with water, brine, dried (sodium sulphate), filtered and concentrated to a white solid. The material was purified by flash chromatography on silica gel eluting with ethyl acetate/heptanes to provide 0.231 g of 4-fluoro-1-[4-(trifluoromethyl)benzyloxy]naphthalene-2-carboxylic acid methyl ester as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07919628B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-5f04db3e5d7d4a2bae766988a2c8f6a8 |
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| Source note | uspto-grants-2011_04 |
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