5-Bromo-benzo(b)thiophene-2-carboxylic acid → (5-Bromo-benzo[b]thiophen-2-yl)-methanol

HRID 1173821

反応式

HRID 1173821 の反応式
[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

反応物 1

HCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acid

生成物 1

HCID 21844218(5-Bromo-benzo[b]thiophen-2-yl)-methanol収率 51.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

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

  1. customQuench by careful addition of water
  2. customPartition between ether and saturated NaHCO3
  3. washwash with water, brine
  4. customdry
  5. concentrationconcentrate
  6. customPurify via column chromatography
  7. 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

関連ノート

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