Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2,2,2-Trifluoroethanol | HCID 6409 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3,4-Difluorobenzaldehyde | HCID 588088 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 20794696 | HCID 20794696 | 80% |
Reaction Steps
To a suspension of sodium hydride (60% dispersion in mineral oil, 0.844 g) in N,N-dimethylfounamide (30.0 mL), 2,2,2-trifluoroethanol (2.11 g) was added at 0° C. and thereafter the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, a solution of 3,4-difluorobenzaldehyde (2.00 g) in N,N-dimethylformamide (10.0 mL) was added and thereafter the mixture was stirred at room temperature for 30 minutes. After adding 1 mol/L hydrochloric acid at 0° C., three extractions were conducted with ethyl acetate. The combined organic layers were passed through a phase separator and thereafter concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=80:20-30:70) to give the titled compound as a colorless oil (2.50 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422240B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-4bde3bc648c24cb29ebd146f210442cd |
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| Source note | uspto-grants-2016_08 |
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