Methanesulfonyl chloride → 2-Iodo-4-nitrobenzyl Methanesulfonate

HRID 541793

反応式

HRID 541793 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 579616812-Iodo-4-nitrobenzyl Methanesulfonate収率 80.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f70d53f84da043fe9c4d78d92e66e455
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

関連ノート

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