Methyl iodide → Methyl 5-iodo-2-methoxybenzoate

HRID 227359Notes

Reaction equation

HRID 227359 reaction equation
CI.[C:3]([O-])([O-])=O.[K+].[K+].[I:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([O-:17])=[O:16].C(OCC)(=O)C>CN(C=O)C>[CH3:3][O:16][C:15](=[O:17])[C:14]1[CH:18]=[C:10]([I:9])[CH:11]=[CH:12][C:13]=1[O:19][CH3:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 210945415-Iodo-2-methoxybenzoate

Product 1

HCID 11011762Methyl 5-iodo-2-methoxybenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (2.40 mL, 38.48 mmol) and K2CO3 (10.60 g, 76.96 mmol) were added to a solution of 5-iodo-2-methoxybenzoate (5.37 g, 19.24 mmol) in DMF (20 mL) and stirred at rt under Ar for 24 h. Upon completion, ethyl acetate was added and the reaction was washed with 1% HCl (2×20 mL), brine (1×), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (3:1 hexane:ethyl acetate) to afford methyl-5-iodo-2-methoxybenzoate (4.93 g, 88%) as a white solid. See, for example, Corey, E. J.; Myers, A. G. J. Am. Chem. Soc. 1985, 107, 5574-5576, which is incorporated by reference in its entirety. 1H NMR (DMSO-d6, 400 MHz) δ 7.90 (d, 1H, J=2.4 Hz), 7.80 (dd, 1H, J=8.8, 2.4 Hz), 6.96 (d, 1H, J=9.0 Hz), 3.81 (s, 3H), 3.79 (s, 3H). 13C NMR (DMSO-d6, 100 MHz) δ 164.7, 158.0, 141.6, 138.5, 122.2, 115.2, 82.1, 55.9, 52.0. HREIMS calculated for C9H9IO3 (M+) 291.9608. found 291.9596.

Workup

  1. washthe reaction was washed with 1% HCl (2×20 mL), brine (1×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-87edd9cf2b164e0e9fd96fe732bc5999
Source dataset
uspto-grants-2009_07
Patent number
US07560488B2

Reaction notes

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