Acetic Acid → 1-Iodo-3,5-dimethoxybenzene

HRID 1003944

반응식

HRID 1003944 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)N.C(O)(=O)C.N([O-])=O.[Na+].[I-:20].[K+]>Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([I:20])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 663013,5-DimethoxyanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 6401791-Iodo-3,5-dimethoxybenzene수율 60.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매3회

반응 조건

온도
80 °C

실험 절차

3,5-Dimethoxyaniline (1.0 g) is suspended in a mixture of hydrochloric acid (3 ml), acetic acid (2 ml) and water (5 ml), and thereto is added dropwise a solution of sodium nitrite (473 mg) in water (5 ml) under ice-cooling over a period of 15 minutes. Ten minutes thereafter, to the mixture is added a solution of potassium iodide (1.62 g) in water (5 ml), and the mixture is warmed to 80° C., and stirred for one hour. The reaction mixture is extracted with diethyl ether, and the extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate), and is recrystallized from ethyl acetate/hexane to give 3,5-dimethoxyiodobenzene (1.05 g), m.p. 73-74° C.

후처리

  1. temperaturecooling over a period of 15 minutes
  2. extractionThe reaction mixture is extracted with diethyl ether
  3. washthe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)
  7. customis recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-d1a45238f9a541beaf9ff645f880e057
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048842

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