反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH3:11][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[CH:4][C:3]=1[F:10]参加物
実験手順
To a solution of 4-bromo-3-fluorobenzaldehyde (5 g, 24.75 mmol) in anhydrous tetrahydrofuran (100 mL) was added methyl magnesium bromide (3 M solution in tetrahydrofuran, 8.21 mL) at −45° C. under the atmosphere of nitrogen then stirred at room temperature. After 2 hours, LC-MS showed the desired product has received. The aqueous of ammonium chloride (15 mL) was added to quench the reaction, and extracted with ethyl acetate (50 mL), combined and concentrated the organic layers. The crude product was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to give 1-(4-bromo-3-fluorophenyl)ethanol (4 g, 78%). LCMS (M+H+) m/z: calcd 217.97. found 218. 1H NMR (300 MHz, CD3OD): δ 7.92-7.87 (m, 1H), 7.23-7.19 (m, 1H), 7.07-7.10 (m, 1H), 4.80 (d, J=6.3 Hz, 1H), 1.41 (t, J=2.7 Hz, 3H).
出典と根拠
- ORDレコード
- ord-86254549ae6742c5aa12c4c86923c28f
- 出典データセット
- uspto-grants-2015_12
- 特許番号
- US09206128B2
関連ノート
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