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

HRID 1030772

Reaktionsgleichung

Reaktionsgleichung von HRID 1030772
[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-30a81e276ecc4c8daf30a647560d7c33
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106957

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