Lithium Bromide → 2-(2-Bromoethyl)-1-methyl-4-nitrobenzene

HRID 351766Notes

Reaction equation

HRID 351766 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH3:17])(=O)=O.[Br-:18].[Li+]>CC(C)=O>[Br:18][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH3:17]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 227144062-(2-Methanesulfonyloxyethyl)-1-methyl-4-nitrobenzene

Product 1

HCID 227143952-(2-Bromoethyl)-1-methyl-4-nitrobenzeneYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2-methanesulfonyloxyethyl)-1-methyl-4-nitrobenzene (4.0 g) and lithium bromide (6.6 g) in acetone (250 mL) was boiled under reflux for 3½ h. The resulting mixture was cooled and filtered. The residue was purified by flash chromatography on silicagel (eluent:ethyl acetate/heptane 1:2) to give the title compound (3.7 g). 1H NMR (DMSO-d6): 2.45 (s, 3H); 3.25 (t, 2H); 3.80 (t, 2H); 7.50 (d, 1H); 8.05 (dd, 1H); 8.15 (d, 1H).

Workup

  1. temperatureunder reflux for 3½ h
  2. temperatureThe resulting mixture was cooled
  3. filtrationfiltered
  4. customThe residue was purified by flash chromatography on silicagel (eluent:ethyl acetate/heptane 1:2)

Sources & evidence

ORD record
ord-4539e3c9bc4f4a6081e43af2804b1253
Source dataset
uspto-grants-2004_06
Patent number
US06743809B2

Reaction notes

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