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

HRID 2377005ノート

反応式

HRID 2377005 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 210994782-Hydroxy-1-(2-iodophenyl)ethanone収率 12%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6acd3799a73b43498eb4b5fc4d1c513a
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

反応ノート

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