Methanesulfonyl chloride → 1-(1-Chloroethyl)-2-nitrobenzene

HRID 1176017

反応式

HRID 1176017 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10](O)[CH3:11])([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.CS([Cl:26])(=O)=O>CN(C)C=O>[Cl:26][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:11]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 978511-(2-Nitrophenyl)ethanol

生成物 1

HCID 137919321-(1-Chloroethyl)-2-nitrobenzene収率 66.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

311 g 1-(2-nitrophenyl)ethanol (XI-1) (95.8% purity, 1.78 mol) are dissolved in 3000 ml dimethyl formamide in a 6 liter three-necked flask equipped with a stirrer, dropping funnel and thermometer. 921.4 g (7.13 mol) diisopropylethylamine are added in a single portion, stirred for 5 minutes, then 612.5 g (5.35 mol) methanesulfonyl chloride are added dropwise between 20 to 35° C. with good cooling. After the reaction has subsided, it is stirred for another 90 hours at room temperature, and the solvent is removed under vacuum. Then the residue dissolved in ethyl acetate, washed 3 times with water, dried over sodium sulfate and the solvent is removed under vacuum. The crude product is purified by column chromatography (silica gel, 9:1 hexane/acetone). 219 g of 1-(1-chloroethyl)-2-nitrobenzene (100% purity by HPLC, 66.2% theoretical yield) are obtained as a brown oil [logP (pH 2.3)=2.87].

後処理

  1. customequipped with a stirrer
  2. stirringit is stirred for another 90 hours at room temperature
  3. customthe solvent is removed under vacuum
  4. dissolutionThen the residue dissolved in ethyl acetate
  5. washwashed 3 times with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed under vacuum
  8. customThe crude product is purified by column chromatography (silica gel, 9:1 hexane/acetone)

出典と根拠

ORDレコード
ord-5a13c381bf824820a3a939bbb99765f2
出典データセット
uspto-grants-2010_11
特許番号
US07842710B2

関連ノート

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