Potassium Acetate → 2-Bromo-3-nitrobenzyl acetate

HRID 1995144

Reaktionsgleichung

Reaktionsgleichung von HRID 1995144
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11]Br.[C:13]([O-:16])(=[O:15])[CH3:14].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(Cl)Cl>[C:13]([O:16][CH2:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Br:1])(=[O:15])[CH3:14]

Komponenten

6

Edukt 2

HCID 517044Potassium AcetateHCID 110663422-Bromo-1-bromomethyl-3-nitrobenzene

Produkt 1

HCID 128530522-Bromo-3-nitrobenzyl acetateAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 2-bromo-1-bromomethyl-3-nitrobenzene (20.2 g, 0.0685 mole), potassium acetate (10.08 g, 0.103 mole), and tetrabutylammonium chloride (1.5 g) in 150 ml of acetonitrile was heated at reflux for six hours. The reaction mixture was cooled, filtered, and extracted with methylene chloride. The extract was evaporated to give a residue which was redissolved in methylene chloride and washed twice with 150 ml portions of saturated aqueous sodium chloride solution. The organic phase was passed through phase separation filter paper and evaporated to give a dark solid. The solid was purified by column chromatography on silica gel, elution with toluene, to give (2-bromo-3-nitrophenyl)methyl acetate as a yellow solid (9.6 g, mp 60°-63°).

Aufarbeitung

  1. temperatureat reflux for six hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. extractionextracted with methylene chloride
  5. customThe extract was evaporated
  6. customto give a residue which
  7. washwashed twice with 150 ml portions of saturated aqueous sodium chloride solution
  8. customThe organic phase was passed through phase separation
  9. filtrationfilter paper
  10. customevaporated
  11. customto give a dark solid
  12. customThe solid was purified by column chromatography on silica gel, elution with toluene

Quellen und Nachweise

ORD-Eintrag
ord-38018cec90f046fcac909737d2075cc3
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04402973

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