Methyl iodide → Methyl 2-bromo-5-iodobenzoate

HRID 1270778Notes

Reaction equation

HRID 1270778 reaction equation
CI.[Br:3][C:4]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[C:14]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([I:13])[CH:11]=[CH:12][C:4]=1[Br:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 50998202Methyl 2-bromo-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (13 g, 91.5 mmol) is added to slurry of 2-bromo-5-iodobenzoic acid (23 g, 70.4 mmol) and K2CO3 (14.6 g, 106 mmol) in DMF (50 mL) at room temperature. After TLC shows complete consumption of the starting material, the reaction is diluted with Et2O and washed three times with a saturated aqueous solution of NaCl. The combined aqueous layers are extracted once with fresh Et2O and once with EtOAc. The organic layers are combined, dried with Na2SO4, filtered and concentrated to an oil. The oil is diluted with a minimal amount of Et2O and filtered through a plug of silica. The silica is rinsed with a 20% ether/hexanes mixture. The eluents are concentrated in vacuo to give 2-bromo-5-iodobenzoic acid methyl ester as a solid.

Workup

  1. customconsumption of the starting material
  2. additionthe reaction is diluted with Et2O
  3. washwashed three times with a saturated aqueous solution of NaCl
  4. extractionThe combined aqueous layers are extracted once with fresh Et2O and once with EtOAc
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. additionThe oil is diluted with a minimal amount of Et2O
  9. filtrationfiltered through a plug of silica
  10. washThe silica is rinsed with a 20% ether/hexanes mixture
  11. concentrationThe eluents are concentrated in vacuo

Sources & evidence

ORD record
ord-35bf1a3fbab84cbc88bbc5244995b002
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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