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

HRID 5552

Reaction equation

HRID 5552 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 149591702,4,6-Tris(bromomethyl)nitrobenzeneYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-728658d230cb49b7815fa4f092792817
Source dataset
uspto-grants-1993_09
Patent number
US05245038

Linked notes

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