HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 86666216, compound → HCID 67776822, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 86666216 | HCID 86666216 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Methyltriphenyliphosphonium bromide | HCID 74505 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67776822 | HCID 67776822 | 43.1% |
Reaction Steps
To a suspension of methyltriphenylphosphonium bromide (3.9 g, 10.92 mmol) in dry THF (20 mL) was added n-butyllithium (6.8 mL, 10.88 mmol) dropwise at −78° C. for 0.5 h, the mixture was stirred for 1 h, and then was added a solution of 4-(4-chloro-3-(trifluoromethoxy)phenoxy)benzaldehyde (2.8 g, 8.84 mmol) in THF (5 mL). The reaction was warmed slowly to room temperature, stirred for overnight, and quenched with water. The aqueous layer was extracted with DCM. The organic phase was dried with anhydrous Na2SO4, concentrated and purified via flash chromatography to afford the title compound (1.2 g, 3.81 mmol, 43.1% yield). LCMS: rt=4.42 min, [M+H+]=315
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-85040bb1eec24052a39ade24a6f223ec |
| Source note | uspto-grants-2014_01 |