Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 2734385 | — |
| Reactant | HCID 10331694 | HCID 10331694 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59553713 | HCID 59553713 | 58% |
Reaction Steps
To a solution of 522 mg (2.5 mmol) 3-(trifluoromethoxy)phenylboronic acid in 10 ml toluene under argon at RT, was added successively 29.7 mg (0.04 mmol) Pd(PPh3)2Cl, 776.5 mg (3.2 mmol) K3PO4.H2O and 500 mg (2.1 mmol) 3-(4-Trifluoromethyl-phenyl)-propionyl chloride (CAS: 539855-79-3). The reaction mixture was heated at 110° C. for 3 h, cooled to RT and ethyl acetate was added. The solution was washed successively with NaHCO3 sat., water and brine. The organic phase was dried over Na2SO4 and evaporated. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.44 g (58%) of the title compound as colorless oil. MS (m/e): 363.0 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07829563B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-9001d2bf93a3423a918473630e9e1240 |
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| Source note | uspto-grants-2010_11 |
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