Methyl iodide → Methyl 3-iodo-4-methyl-5-nitrobenzoate

HRID 446221Notes

Reaction equation

HRID 446221 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:15][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]([CH3:11])=[C:2]([I:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 596277773-Iodo-4-methyl-5-nitrobenzoic acid

Product 1

HCID 24728110Methyl 3-iodo-4-methyl-5-nitrobenzoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-iodo-4-methyl-5-nitro-benzoic acid (16.06 g, 52.3 mmol) in acetone (300 mL) was added K2CO3 (14.46 g, 104.6 mmol) followed by methyl iodide ((3.91 mL, 62.76 mmol). The reaction mixture was stirred at 40° C. overnight, then cooled to room temperature and partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to provide 16.5 g (98%) of 3-iodo-4-methyl-5-nitro-benzoic acid methyl ester.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-846b869706134fd28e8d18aa2de0e38b
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Reaction notes

Loading…