HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 5-(2,2-difluoroethoxy)-2-nitrobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,2-Difluoroethan-1-ol | HCID 136187 | — |
| Reactant | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | HCID 4571243 | — |
| Reactant | 5-Fluoro-2-nitrobenzoic acid methyl ester | HCID 5152049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 5-(2,2-difluoroethoxy)-2-nitrobenzoate | HCID 59587324 | 92.5% |
Reaction Steps
8.53 g of 2,2-difluoroethanol are added to a solution of 17.31 g of methyl 5-fluoro-2-nitrobenzoate, 9.64 g of NEt3 and 32.71 g of 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane in 250 ml of anhydrous THF. The mixture is stirred at AT for 30 min. The solvent is evaporated under reduced pressure. Water is added and extraction is carried out with AcOEt. The extract is washed with a 1N aqueous HCl solution, with water and then with a saturated NaCl solution. It is dried over MgSO4 and filtered, and the solvent is evaporated under reduced pressure to give 21 g of the expected product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846654B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-6a6caacef79c480cb678629b6f435790 |
| Source note | uspto-grants-2014_09 |