Methanol → (3-Bromo-5-fluorophenyl)methanol
反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].O1CCCC1.B.CO>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([F:11])[CH:10]=1参加物
6
反応条件
- 温度
- 0 °C
実験手順
3-Bromo-5-fluorobenzoic acid (1.0 g, 4.52 mmol) was suspended in tetrahydrofuran (8 mL) and cooled to 0° C. To this solution was added borane tetrahydrofuran complex (1 M in tetrahydrofuran, 9 mL, 9.0 mmol) cautiously over 15 min. The reaction mixture was allowed to warm to room temperature overnight. The mixture was cooled to 0° C., treated with excess methanol, diluted with ethyl acetate, washed with 1 N sodium hydroxide (2×), then brine (2×), dried over sodium sulfate, and concentrated to afford 0.88 g (95%) as a white powder. 1H-NMR (CDCl3, 500 MHz) 7.29 (s, 1H), 7.16 (d, J=7.9 Hz, 1H), 7.03 (d, J=9.2 Hz, 1H), 4.66 (s, 2H).
後処理
- temperatureto warm to room temperature overnight
- temperatureThe mixture was cooled to 0° C.
- washwashed with 1 N sodium hydroxide (2×)
- dry with materialbrine (2×), dried over sodium sulfate
- concentrationconcentrated
- customto afford 0.88 g (95%) as a white powder
出典と根拠
- ORDレコード
- ord-1ce982a56fdd4bfd8710c0853567e76c
- 出典データセット
- uspto-grants-2013_02
- 特許番号
- US08383821B2
反応ノート
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