N-bromobutanimide → 1-(Bromomethyl)-2,5-difluoro-4-nitrobenzene

HRID 515305

Reaktionsgleichung

Reaktionsgleichung von HRID 515305
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimide2×HCID 2306581,4-Difluoro-2-methyl-5-nitrobenzene

Produkt 1

HCID 534033971-(Bromomethyl)-2,5-difluoro-4-nitrobenzeneAusbeute 220,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysator2×HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

1,4-Difluoro-2-methyl-5-nitrobenzene (1 g) was dissolved in chlorobenzene (6 mL) and N-bromosuccinimide (1.54 g) added followed by benzoyl peroxide (0.2 g). The reaction mixture was stirred at reflux for 2.5 hours then additional benzoyl peroxide (0.2 g) and N-bromosuccinimide (1.54 g) were added. The reaction was refluxed for 2 hours then was cooled to room temperature, quenched with water and extracted with dichloromethane (3×). The combined organics were dried and concentrated under reduced pressure. The oil obtained was triturated with diethyl ether, filtered and the filtrate concentrated under reduced pressure to yield the title compound (3.21 g).

Aufarbeitung

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction was refluxed for 2 hours
  3. customquenched with water
  4. extractionextracted with dichloromethane (3×)
  5. customThe combined organics were dried
  6. concentrationconcentrated under reduced pressure
  7. customThe oil obtained
  8. customwas triturated with diethyl ether
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-502793d67fcb49f4b86ae129b0caa852
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

Verknüpfte Notizen

Wird geladen…