Methanol → 2-(2-Fluoro-5-nitrophenyl)ethanol

HRID 64344ノート

反応式

HRID 64344 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12](O)=[O:13].CO>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

参加物

4

反応物 2

HCID 887MethanolHCID 8493592-(2-Fluoro-5-nitrophenyl)acetic acid

生成物 1

HCID 248284032-(2-Fluoro-5-nitrophenyl)ethanol収率 86.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-(2-fluoro-5-nitrophenyl)acetic acid (2.0 g, 10 mmol) in THF (50 mL) was added borane dimethyl sulfide complex solution (4.0 g, 25 mmol). The reaction was warmed to 60° C. stirred for about 12 hr. After cooling down to RT, CH3OH (20 mL) was slowly added to the reaction, concentrated under reduced pressure to remove solvent. The residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1) to afford the product as a colorless oil (1.6 g, 86.1%). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (t, J=3.2, 6.4 Hz, 1 H), 8.19-8.14 (m, 1 H), 8.45 (t, J=9.2 Hz, 1 H), 4.80 (t, J=5.6 Hz, 1 H), 3.66 (dt, J=5.6, 6.4 Hz, 1 H), 2.86 (t, J=6.4 Hz, 2 H). MS (ESI) m/e [M+1]+ 186.

後処理

  1. temperatureAfter cooling down to RT
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. customThe residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1)

出典と根拠

ORDレコード
ord-6531ebd2a299490dbb8aedcb697991e7
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

反応ノート

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