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

HRID 1176017

Reaktionsgleichung

Reaktionsgleichung von HRID 1176017
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 137919321-(1-Chloroethyl)-2-nitrobenzeneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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].

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5a13c381bf824820a3a939bbb99765f2
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842710B2

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