Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Phenylmaleic anhydride | HCID 99174 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68458790 | HCID 68458790 | 86.5% |
Reaction Steps
To a stirred solution of phenylmaleic anhydride (18.7 g, 0.107 mol) in acetonitrile (180 ml) at 0° C. (ice/water/sodium chloride bath—temperature of the bath −10° C.), was added CsF (18.6 g, 0.127 mol), followed by the drop-wise addition of CF3SiMe3 (18.58 ml, 0.127 mol), under nitrogen. The reaction mixture was stirred for 1 h, and was then diluted with diethyl ether and extracted with 2M sodium hydroxide (200 ml). The separated aqueous layer was acidified to pH=1 by the addition of conc. hydrochloric acid. This mixture was extracted with dichloromethane. The separated organic layer was dried (Na2SO4), and the solvent was evaporated in vacuo to yield D1 (22.6 g, 86%) as a mixture of isomers (80/11 ratio by LCMS). C11H7F3O3 requires 244; Found 243 (M-H−).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422296B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-f216a84fa29143b4b9accd83c3799390 |
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| Source note | uspto-grants-2016_08 |
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