5-Bromo-benzo(b)thiophene-2-carboxylic acid → (5-Bromo-benzo[b]thiophen-2-yl)-methanol
反応式
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([C:9](O)=[O:10])=[CH:8][C:4]=2[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([CH2:9][OH:10])=[CH:8][C:4]=2[CH:3]=1参加物
3
反応条件
- 温度
- 0 °C
実験手順
Dissolve 5-bromo-benzo[b]thiophene-2-carboxylic acid (21.2 g, 82.5 mmol) in THF (150 mL). Cool to 0° C. with an ice bath. Add 2M BH3 dimethyl sulfide complex in THF (82.5 mL). Stir to room temperature over 2 hours. Quench by careful addition of water. Partition between ether and saturated NaHCO3, wash with water, brine, dry, and concentrate. Purify via column chromatography eluting with 3:1 hexanes:ethyl acetate to afford a white solid (10.3 g): 1H NMR (CDCl3) δ 7.87 (m, 1H), 7.67 (d, 1H), 7.41 (dd, 1H), 7.15 (m, 1H), 4.94 (d, 2H), 1.91 (t, 1H).
後処理
- customQuench by careful addition of water
- customPartition between ether and saturated NaHCO3
- washwash with water, brine
- customdry
- concentrationconcentrate
- customPurify via column chromatography
- washeluting with 3:1 hexanes
出典と根拠
- ORDレコード
- ord-47624e7d3ee545ba976f65ea6d9ccd53
- 出典データセット
- uspto-grants-2010_11
- 特許番号
- US07834194B2
反応ノート
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