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

HRID 1700995노트

반응식

HRID 1700995 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e838b16678bf48e7a891784cb3c9316b
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350907B1

반응 노트

불러오는 중…