Hydrochloric Acid → 3-Bromo-2,4-dichloro-5-fluoronitrobenzene

HRID 1761644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1761644
[Br:1][C:2]1[C:8]([Cl:9])=[C:7]([F:10])[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[C:3]=1N.C(ON=O)(C)(C)C.[ClH:21]>C(#N)C>[Br:1][C:2]1[C:3]([Cl:21])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[C:7]([F:10])[C:8]=1[Cl:9]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 137487952-Bromo-3-chloro-4-fluoro-6-nitroaniline

Produkt 1

HCID 137487963-Bromo-2,4-dichloro-5-fluoronitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of anhydrous cupric chloride (147 g) and 2-bromo-3-chloro-4-fluoro-6-nitroaniline (235.6 g) in anhydrous acetonitrile (1.5 litter) was added tert-butylnitrite (135.2 g) at 60° C. during 70 minutes. The reaction mixture was poured into ice-chilled diluted hydrochloric acid (1.5 litter) and extracted with benzene. The organic layer was successively washed with ice-chilled diluted hydrochloric acid and water saturated with sodium chloride, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by distillation to give the title compound (218.8 g), bp 78°-117° C./2 mmHg. The oil was crystallized from methanol to give yellow prisms, mp 65.5°-67.5° C.

Aufarbeitung

  1. additionThe reaction mixture was poured into ice-
  2. extractionextracted with benzene
  3. washThe organic layer was successively washed with ice-
  4. temperaturechilled diluted hydrochloric acid and water saturated with sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationThe resulting residue was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-5dfc557fcc044fec826692726a7e466f
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04826982

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