関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Vinyl Acetate | HCID 7904 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Methyl 3-bromo-4-hydroxybenzoate | HCID 4778958 | — |
| 触媒 | Chloro(1,5-cyclooctadiene)iridium(I) dimer | HCID 6436381 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | HCID 117933568 | HCID 117933568 | 65.6% |
反応手順
To a solution of methyl 3-bromo-4-hydroxy-benzoate (1.00 g, 4.33 mmol, 1.00 eq) in toluene (15.00 mL) were added vinyl acetate (745.54 mg, 8.66 mmol, 2.00 eq), Chloro(1,5-cyclooctadiene)iridium(I) dimer (29.08 mg, 43.30 umol, 0.01 eq) and Na2CO3 (229.47 mg, 2.17 mmol, 0.50 eq). The mixture was stirred at 100° C. for 16 hr under N2 protection. TLC detected the reaction was complete, the solvent was evaporated, the residue was purified by chromatography (silica gel, eluting with PE:EA=10:1) to afford product methyl 3-bromo-4-vinyloxy-benzoate (730.00 mg, 2.84 mmol, 65.58% yield) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, J=1.76 Hz, 1H), 7.99 (dd, J=8.53, 2.01 Hz, 1H), 7.06 (d, J=8.53 Hz, 1H), 6.65 (dd, J=13.80, 6.02 Hz, 1H), 4.98 (dd, J=13.80, 2.01 Hz, 1H), 4.70 (dd, J=5.90, 1.88 Hz, 1H), 3.93 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09339510B2 |
|---|
| 出典データセット | uspto-grants-2016_05 |
|---|
| ORD ID | ord-9d7441a074574789939fafd2e236f0fa |
|---|
| 出典メモ | uspto-grants-2016_05 |
|---|