Methyl iodide → Methyl 4-chloro-3-nitrobenzoate

HRID 1370099Notes

Reaction equation

HRID 1370099 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 73204-Chloro-3-nitrobenzoic acidHCID 11430Potassium Carbonate

Product 1

HCID 735797Methyl 4-chloro-3-nitrobenzoateYield 88.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-chloro-3-nitrobenzoic acid (10 g) and potassium carbonate (7.54 g) in N,N-dimethylformamide (100 mL) was added methyl iodide (3.24 mL) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was diluted with ethyl acetate and washed successively with 1 N-hydrochloric acid, water, an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual solid was washed with diisopropyl ether to give methyl 4-chloro-3-nitrobenzoate (9.51 g) as a yellow solid.

Workup

  1. washwashed successively with 1 N-hydrochloric acid, water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. washThe residual solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-d51a2e06b0e24465a9bef225d096c71b
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

Loading…