Nitric Acid → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

HRID 400553

Reaktionsgleichung

Reaktionsgleichung von HRID 400553
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 967432-Bromo-5-fluorotoluene

Produkt 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneAusbeute 104,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Combine 1-bromo-4-fluoro-2-methylbenzene (30.0 g, 159 mmol) in concentrated sulfuric acid (100 mL), cool to about −5° C., and treat dropwise with nitric acid (11.00 mL, 174 mmol) over 20 minutes. Allow reaction mixture to warm to RT and stir for 30 min. Pour onto crushed ice with stiffing and partition with tert-butyl methyl ether (MTBE) (200 mL). Separate the aqueous layer and extract with MTBE (2×50 mL). Combine organic layers, dry and concentrate under reduced pressure to provide 1-bromo-4-fluoro-2-methyl-5-nitrobenzene as an orange-colored viscous oil (39.0 g).

Aufarbeitung

  1. customAllow reaction mixture
  2. additionPour
  3. customonto crushed ice with stiffing
  4. custompartition with tert-butyl methyl ether (MTBE) (200 mL)
  5. customSeparate the aqueous layer
  6. extractionextract with MTBE (2×50 mL)
  7. customCombine organic layers, dry
  8. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-11409640bb6745f38880db83dafaac01
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741911B2

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