Methane → 2-Bromo-3-nitrobenzoyl chloride

HRID 1491621

Reaktionsgleichung

Reaktionsgleichung von HRID 1491621
[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O.C>CC1C=CC=CC=1>[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Komponenten

5

Edukt 3

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 684522-Bromo-3-nitrobenzoic acid

Produkt 1

HCID 2229532-Bromo-3-nitrobenzoyl chlorideAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 414 parts of 2-bromo-3-nitrobenzoic acid in 653 parts of methylbenzene there were added 440 parts of thionyl chloride. The whole was refluxed for 6 hours, cooled and left overnight. The reaction mixture was treated with activated charcoal, filtered over diatomaceous earth and evaporated. The residual oil was triturated with 396 parts of hexane (2×). The product was filtered off, washed with hexane and dried, yielding 363 parts (81.7%) of 2-bromo-3-nitrobenzoyl chloride (interm. 3).

Aufarbeitung

  1. temperatureThe whole was refluxed for 6 hours
  2. temperaturecooled
  3. filtrationfiltered over diatomaceous earth
  4. customevaporated
  5. customThe residual oil was triturated with 396 parts of hexane (2×)
  6. filtrationThe product was filtered off
  7. washwashed with hexane
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dc78b28494bc463ca731b611c6d79bae
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371079

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