Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-(Trifluoromethyl)benzaldehyde | HCID 67996 | — |
| Reactant | 1-(Benzyloxy)-2-bromobenzene | HCID 561828 | — |
| Reactant | HCID 178418244 | HCID 178418244 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67460497 | HCID 67460497 | 82% |
Reaction Steps
In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 4.0 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (2.6 g, 9.9 mmol) in THF (100 mL) at −78° C. and the reaction mixture was stirred at the same temperature for 30 minutes. To this solution, 4-trifluoromethylbenzaldehyde (1.6 g, 9.0 mmol) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for two hours, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.6 g, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08048897B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-b5db9d4352b54f1bb8057fc779e900fa |
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| Source note | uspto-grants-2011_11 |
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