Methyl iodide → Methyl 4-iodobenzoate

HRID 1264228Notes

Reaction equation

HRID 1264228 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120854-Iodobenzoic acid

Product 1

HCID 69273Methyl 4-iodobenzoateYield 83.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-iodobenzoic acid (9.92 g, 40 mmol) in DMF (80 mL) is added potassium carbonate (5.8 g, 42 mmol) and iodomethane (2.6 mL, 42 mmol). The resulting mixture is stirred for 17 hours, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The crude solid is recrystallized in ethyl acetate/hexane to give 8.74 g of title compound. 1H NMR (CDCl3) δ 3.91 (s, 3H), 7.74 (d, J=8 Hz, 2H), 7.80 (d, J=8 Hz, 2H). MS (EI) m/z 262 (M+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude solid is recrystallized in ethyl acetate/hexane

Sources & evidence

ORD record
ord-38d10853b43d477198b9061f06b11dd4
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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