Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,2-Difluoro-4-nitrobenzene | HCID 123053 | — |
| Reactant | 4,4-dimethyl-1,4-azasilinane hydrochloride | HCID 67215837 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 89501539 | HCID 89501539 | 70% |
Reaction Steps
To a solution of 4,4-dimethyl-1,4-azasilinane hydrochloride 4 (500 mg, 3.85 mmol) in EtOAc (15 mL), triethylamine (1.3 mL, 9.63 mmol) is added and stirred at 25° C. for 10 min. The reaction mixture is cooled to 0° C. and 3,4-difluoronitrobenzene (612 mg, 3.85 mmol) is added drop wise and allowed to stir at 25° C. for 6 h. Water is then added and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×10 mL) and the solvent is removed under reduced pressure. The product is purified by column chromatography using hexane-EtOAc mixtures and a crystalline yellow solid 9 (721 mg) is obtained in 70% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09233989B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-17d4a825683f42adb6d6ab8cc3eb23fd |
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| Source note | uspto-grants-2016_01 |
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