1-Chloro-4-nitrobenzene → Methyl 5-chloro-2-nitrobenzeneacetate

HRID 1252587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252587
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CN([S+](N(C)C)N(C)C)C.C[Si-](F)(F)(C)C.BrBr.S(=O)(O)[O-:30].[Na+].C1[CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:35][C:36]([O:37][CH3:38])=[O:30])([O-:10])=[O:9]

Komponenten

7

Edukt 5

HCID 74741-Chloro-4-nitrobenzeneHCID 8028TetrahydrofuranHCID 24408BromineHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 13265167Methyl 5-chloro-2-nitrobenzeneacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1.576 g (10 mmol) of 4-chloronitrobenzene and 1.68 mL (10.22 mmol) of carbomethyoxymethyltrimethylsilane in anhydrous THF was added 2.751 g (10 mmol) of TASF in 5 mL of acetonitrile at -78° C. The mixture was stirred for 7 hrs at that temperature, and 0.50 mL (9.70 mmol) of bromine was added dropwise. Stirring was continued for 1 hr, and saturated sodium bisulfite was added. The product was extracted into ether and isolated by chromatography on silica using 30% ether/hexane as solvent. The yield was 1.15 g (50%) product, which was an oil. The product was analyzed by infrared spectroscopy and nuclear magnetic resonance spectroscopy.

Aufarbeitung

  1. additionwas added dropwise
  2. extractionThe product was extracted into ether
  3. customisolated by chromatography on silica using 30% ether/hexane as solvent

Quellen und Nachweise

ORD-Eintrag
ord-b962bc8d73b5476ba2995628cdf5f50b
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743690

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