関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Nitrogen | HCID 947 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Methyl 4-bromocinnamate | HCID 816774 | — |
| 反応物 | 4-(4-Trifluoromethoxyphenyl)phenol | HCID 12008734 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoate | HCID 54757818 | 85% |
反応手順
A solution of methyl (E)-3-(4-bromophenyl)-2-propenoate (99) (0.500 g, 2.07 mmol) and 4-(trifluoromethoxy)phenylboronic acid (44) (0.612 g, 2.97 mmol) in dioxane (40 mL) and aqueous K2CO3 (2M, 10 mL, 20 mmol) was purged with N2. Pd(dppf)Cl2 (0.050 g, 0.06 mmol) was added and the solution was refluxed under N2 for 1 h. The dioxane was removed and the residue was extracted with EtOAc, the organic fraction was dried and the solvent was removed. Column chromatography of the residue on silica gel using gradient elution (hexanes to CH2Cl2) gave methyl (2E)-3-[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]-2-propenoate (100) (0.567 g, 85%) as a white solid: mp 98-100° C.; 1H NMR (CDCl3) δ 7.73 (d, J=16.0 Hz, 1H), 7.56-7.63 (m, 6H), 7.30 (dd, J=8.8, 0.9 Hz, 2H), 6.48 (d, J=16.0 Hz, 1H), 3.82 (s, 3H). APCI MS m/z 323 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09198913B2 |
|---|
| 出典データセット | uspto-grants-2015_12 |
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| ORD ID | ord-af23c11d57c3404a979a89cdabf7813c |
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| 出典メモ | uspto-grants-2015_12 |
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