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

HRID 64344노트

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HRID 64344 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 248284032-(2-Fluoro-5-nitrophenyl)ethanol수율 86.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6531ebd2a299490dbb8aedcb697991e7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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