Water → 2-Hydroxy-1-(2-iodophenyl)ethanone

HRID 1351690노트

반응식

HRID 1351690 반응식
I[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C([I:18])C=CC=1.[OH2:30]>CS(C)=O>[OH:30][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[I:18])=[O:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 138307Ethanone, 2-iodo-1-phenyl-HCID 21918218Hydroxy tosyloxy iodobenzene

생성물 1

HCID 210994782-Hydroxy-1-(2-iodophenyl)ethanone수율 12%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 2-iodoacetophenone (1 g, 4.1 mmol) and hydroxy(tosyloxy)iodobenzene (1.86 g, 4.92 mmol) in dimethylsulfoxide:water (40 mL:2 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to give 2-hydroxy-1-(2-iodophenyl)ethanone (126 mg, 12%). δH (400 MHz, d6 DMSO): 7.94 (1H, dd, J=0.9, 7.8 Hz), 7.54 (1H, dd, J=1.8, 7.7 Hz), 7.49–7.45 (1H, m), 7.25–7.21 (1H, m), 5.37 (1H, t, J=6.0 Hz), 4.52 (2H, d, J=6.0 Hz).

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 40% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-a2f38adddfc94a3e9f802d1ed160aa83
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217740B2

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