Lithium Chloride → 2-Chloro-1,3-dimethyl-5-nitrobenzene

HRID 2256479Notes

Reaction equation

HRID 2256479 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[CH3:17])(=O)=O.[Cl-:20].[Li+]>CN(C=O)C>[Cl:20][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[CH3:17]

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 226621252,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonate (8.54 g) and 3.63 g of lithium chloride in 40 ml DMF are heated at 150° for four hours. Solvent is then evaporated, the residue stirred with water and ethyl acetate, filtered, and the filtrate separated. The ethyl acetate is then dried, filtered and stripped, and the residue chromatographed on silica gel with 98:2 hexane:ethyl acetate, affording 4-chloro-3,5-dimethyl-nitrobenzene. NMR (CDCl3): δ 2.5 (6H,s), 7.9 (2H,s).

Workup

  1. customSolvent is then evaporated
  2. filtrationfiltered
  3. customthe filtrate separated
  4. dry with materialThe ethyl acetate is then dried
  5. filtrationfiltered
  6. customthe residue chromatographed on silica gel with 98:2 hexane

Sources & evidence

ORD record
ord-88340db264bc49c4a5b6dca080395109
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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