Water → 2,4,6-Tris(bromomethyl)nitrobenzene

HRID 1086946

Reaktionsgleichung

Reaktionsgleichung von HRID 1086946
[Br:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][Br:10])[CH:6]=[C:5]([CH2:11][Br:12])[CH:4]=1.F[B-](F)(F)F.[O:18]=[N+:19]=[O:20].O>CC#N>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][Br:12])[CH:6]=[C:7]([CH2:9][Br:10])[C:8]=1[N+:19]([O-:20])=[O:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5302581,3,5-Tris(bromomethyl)benzeneHCID 11073463Nitronium tetrafluoroborate

Produkt 1

HCID 149591702,4,6-Tris(bromomethyl)nitrobenzeneAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracted with CH2Cl2. The CH2Cl2 extracts were washed with 10% NaHCO3, dried (Na2SO4) and solvents removed to afford 4.86 g (86%) of the desired nitro compound 27: NMR (CDCl3) 4.5 (s,6,--CH2Br), 7.55 (s,--C6H2).

Aufarbeitung

  1. extractionthe mixture extracted with CH2Cl2
  2. washThe CH2Cl2 extracts were washed with 10% NaHCO3
  3. dry with materialdried (Na2SO4) and solvents
  4. customremoved

Quellen und Nachweise

ORD-Eintrag
ord-73e7bbbe8fda4cd2885f2046a6cc5970
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05032677

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