Water → 3-Iodo-3'-(trifluoromethyl)biphenyl-4-ol

HRID 1619622ノート

反応式

HRID 1619622 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[I:18]N1C(=O)CCC1=O.O>C(O)(=O)C>[I:18][C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=2)[CH:14]=[CH:13][C:12]=1[OH:15]

参加物

5

反応物 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 200995974-(3-Trifluoromethylphenyl)phenol

生成物 1

HCID 580422843-Iodo-3'-(trifluoromethyl)biphenyl-4-ol収率 39.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 3′-(trifluoromethyl)biphenyl-4-ol (Preparation 1, 2.17 g, 9.11 mmol) in acetic acid (20 mL) at 0° C. was added N-iodosuccinimide (2.05 g, 9.11 mmol). The reaction was allowed to warm to room temperature and stirred for 48 hours before the addition of water (20 mL). The reaction mixture was extracted with dichloromethane (2×20 mL) and the combined extracts were washed with saturated aqueous sodium thiosulfate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution) to afford the title compound (1.30 g, 39%).

後処理

  1. extractionThe reaction mixture was extracted with dichloromethane (2×20 mL)
  2. washthe combined extracts were washed with saturated aqueous sodium thiosulfate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution)

出典と根拠

ORDレコード
ord-e79e6675d1bb47ee9f6ca1128ea2c540
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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