Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4'-Fluoroacetophenone | HCID 9828 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | 4-Amino-1,3-dihydro-2-benzofuran-1-one | HCID 12284649 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178463257 | HCID 178463257 | 88% |
Reaction Steps
To a solution of 4-aminoisobenzofuran-1(3H)-one (1 g, 6.7 mmol) and 1-(4-fluorophenyl)ethanone (1.4 g, 10.1 mmol) in toluene (35 mL) was added anhydrous magnesium sulfate (8.8 g, 73.7 mmol) and acetic acid (0.2 mL) at room temperature under N2. The reaction mixture was then stirred at 120° C. for 36 hr. The reaction mixture was cooled to 90° C. and filtered. After filter cake was washed with acetonitrile, the filtrates were combined and evaporated to dryness to obtain yellow solid, which was washed by petroleum ether to obtain the title compound as a white solid (1.58 g, yield 88%). LC-MS (ESI) m/z: 270 (M+1)+ 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.30 (s, 3H), 5.16 (s, 2H), 7.00-7.02 (d, J=7.6 Hz, 1H), 7.13-7.18 (m, 2H), 7.51-7.56 (t, J=7.6 Hz, 1H), 7.66-7.69 (d, J=7.6 Hz, 1H), 7.99-8.03 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08999987B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-fca144a0f09a40c498e2c525ee98bf8e |
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| Source note | uspto-grants-2015_04 |
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