Sodium Iodide → 1-((4-(2-Iodoethyl)phenoxy)methyl)benzene

HRID 490066

반응식

HRID 490066 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-:30].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][I:30])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3017260p-(Benzyloxy)phenethyl alcohol

생성물 1

HCID 104272231-((4-(2-Iodoethyl)phenoxy)methyl)benzene

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-(4-benzyloxy-phenyl)-ethanol (78.72 g, 0.34 mol) in methylene chloride (400 ml) is added triethylamine (67.3 ml, 0.44 mol, 1.4 eq), then at 0° C. is added mesylchloride (34.8 ml, 0.44 mol, 1.3 eq). The reaction mixture is stirred at 0° C. for 30 minutes and allowed to rise to room temperature. The reaction mixture is extracted with methylene chloride (2×300 ml), the combined organic layers are then washed with brine (2×300 ml) and concentrated under vacuum. To the crude product in solution in ethyl acetate (600 ml) is added sodium iodide (67.2 g, 0.44 mol, 1.3 eq) and the reaction mixture is stirred under reflux for 6 hours. After filtration, the organic layer is washed with brine (3×400 ml), dried with Na2SO4, filtered and concentrated under vacuum. 1-Benzyloxy-4-(2-iodo-ethyl)-benzene is isolated after crystallization with diethyl ether (116.5 g, 86%).

후처리

  1. customto rise to room temperature
  2. extractionThe reaction mixture is extracted with methylene chloride (2×300 ml)
  3. washthe combined organic layers are then washed with brine (2×300 ml)
  4. concentrationconcentrated under vacuum
  5. stirringthe reaction mixture is stirred
  6. temperatureunder reflux for 6 hours
  7. filtrationAfter filtration
  8. washthe organic layer is washed with brine (3×400 ml)
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-80e18cd9d0e5467a885d546509bdecc7
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528120B2

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