Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 4-hydroxy-5-nitro-2-(trifluoromethyl)benzoate | HCID 58376066 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67330864 | HCID 67330864 | 52.2% |
Reaction Steps
Methyl 4-hydroxy-5-nitro-2-(trifluoromethyl)benzoate (3.0 g) was dissolved in N,N-dimethyl-formamide (50 ml), and thereto were added benzyl bromide (2.3 g) and potassium carbonate (2.3 g), and the mixture was stirred at 80° C. for 6 hours. The reaction mixture was cooled, and water was added thereto. The mixture was extracted with ethyl acetate, and the organic layer was washed twice with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=8:1→5:1→3:1) to give methyl 4-(benzyloxy)-5-nitro-2-(trifluoromethyl)benzoate (2.1 g), which was treated in a similar manner to Reference Example 5 to give the title compound (1.9 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08389511B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-c3f4c4e6aa054e919a99adff032f64fc |
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| Source note | uspto-grants-2013_03 |
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