Carbon Tetrachloride → 1-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzene

HRID 1654543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654543
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)Cl>O>[Br:13][CH2:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]([CH3:12])[C:2]=1[Cl:1]

Komponenten

6

Edukt 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzene

Produkt 1

HCID 189972501-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzeneAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 129 g of 2-chloro-1,3-dimethyl-5-nitrobenzene, 125 g of 1-bromo-2,5-pyrrolidinedione, 12 g of dibenzoyl peroxide and 1200 ml of tetrachloromethane was stirred for 2 hours at reflux temperature using a water separator. Twice there was added an extra portion of 20 g of dibenzoyl peroxide during a refiuxing period of 29 hours. After cooling, the reaction mixture was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50). The eluent of the desired fraction was evaporated, yielding 130 g (70.2%) of 1-(bromomethyl)-2-chloro-3-methyl-5-nitrobenzene (interre. 5).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50)
  8. customThe eluent of the desired fraction was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e060d453da44c858e9f06c6b760df44
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407961

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