Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Benzyl Chloride | HCID 7503 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sulfolane | HCID 31347 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 89704773 | HCID 89704773 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Solvent | Hexamethylphosphoramide | HCID 12679 | — |
| Solvent | 2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- | HCID 81646 | — |
| Product | HCID 89704778 | HCID 89704778 | — |
Reaction Steps
5-(Benzyloxy)-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid can be protected by acid or hydroxyl protection reagent (such as BnBr, BnCl) at ambient temperature in the presence of base (includes Na2CO3, K2CO3, NaHCO3, KHCO3, t-BuOK, t-BuONa) in appropriate inert solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer acetone and methyl ethyl ketone). The reaction proceeds for several hours (3-12 h, prefer 5-10 h). Benzyl 5-(benzyloxy)-3,4-difluoro-2-((2-fluorophenyl)amino)benzoate is obtained after conventional workup.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09290468B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-f42bdeda6bba4ae2a15c84eeb83b4b32 |
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| Source note | uspto-grants-2016_03 |
|---|