Iodine → 4-Iodo-1-(3-methoxyphenyl)-2-methylbenzene

HRID 1700995ノート

反応式

HRID 1700995 の反応式
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[C:4]([CH3:16])[CH:3]=1.[I:17]I.N(OCCC(C)C)=O>C1(C)C=CC=CC=1>[I:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[C:4]([CH3:16])[CH:3]=1

参加物

5

反応物 3

HCID 807IodineHCID 8053Isoamyl NitriteHCID 183192763'-Methoxy-2-methyl[1,1'-biphenyl]-4-amine

生成物 1

HCID 183192524-Iodo-1-(3-methoxyphenyl)-2-methylbenzene収率 74.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
90 °C

実験手順

A stirred solution of 4-amino-1-(3-methoxyphenyl)-2-methylbenzene (5.0 gm 23.4 mmol) and iodine (2.97 gm, 25.8 mmol) in toluene (120 mL) was heated to 50° C. and a solution of iso-amyl nitrite (3.46 mL, 25.8 mmol) in toluene (50 mL) was added. The mixture was heated at 90° C. for 2 h and cooled. The toluene was removed under reduced pressure and the residue was dissolved in dichloromethane and washed with excess 5% aqueous sodium metabisulphite to remove iodine. The organic solution was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by repeated flash chromatography (first column gradient elution with hexane:ethyl acetate starting with neat hexane; second column eluted with hexane) to give 4-iodo-1-(3-methoxyphenyl)-2-methylbenzene as a pale orange oil (5.63 gm, 74%).

後処理

  1. temperaturecooled
  2. customThe toluene was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with excess 5% aqueous sodium metabisulphite
  5. customto remove iodine
  6. dry with materialThe organic solution was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by repeated flash chromatography (first column gradient elution with hexane:ethyl acetate starting with neat hexane; second column eluted with hexane)

出典と根拠

ORDレコード
ord-e838b16678bf48e7a891784cb3c9316b
出典データセット
uspto-grants-2002_02
特許番号
US06350907B1

反応ノート

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