Methanesulfonyl chloride → 2-Iodo-4-nitrobenzyl Methanesulfonate

HRID 541793

반응식

HRID 541793 반응식
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12].C(N(CC)C(C)C)(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[I:1])(=[O:25])=[O:24]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 279258(2-Iodo-4-nitrophenyl)methanol

생성물 1

HCID 579616812-Iodo-4-nitrobenzyl Methanesulfonate수율 80.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2-iodo-4-nitrophenyl)methanol (6.01 g, 21.5 mmol) in methylene chloride (50 mL) was added N,N-diisopropylethylamine (7.50 mL, 43.1 mmol) and methanesulfonyl chloride (1.83 mL, 23.7 mmol) at 0° C. The reaction solution was stirred at same temperature for 2 hours. The reaction was quenched with water, and aqueous layer was extracted with DCM once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated The crude product was purified by flash column chromatography to give the desired product (6.15 g, 80%). LCMS calculated for C8H91NO5S (M+H)+: m/z=358.0.

후처리

  1. customThe reaction was quenched with water, and aqueous layer
  2. extractionwas extracted with DCM once
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated The crude product
  7. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-f70d53f84da043fe9c4d78d92e66e455
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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