Potassium Iodide → Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate

HRID 1661958Notes

Reaction equation

HRID 1661958 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]([CH3:18])=[C:6]([CH:11]=[CH:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[C:7]([O:9][CH3:10])=[O:8].[CH3:19][O:20][CH2:21][CH2:22]Br.[I-].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:3][C:4]1[C:5]([CH3:18])=[C:6]([CH:11]=[CH:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 18694846Methyl 3-hydroxy-4-methanesulfonyl-2-methylbenzoate

Product 1

HCID 66755969Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of sodium hydride (60%, 22.0 mg, 5.32 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added methyl 3-hydroxy-2-methyl-4-(methylsulfonyl)benzoate (1 g, 4.09 mmol) under nitrogen atmosphere at room temperature. After stirring for 30 minutes, 2-bromoethyl methyl ether (1.13 g, 8.18 mmol) and potassium iodide in a catalytic amount were added thereto, and the reaction solution was stirred at 60° C. for 12 hours. 200 mL of ethyl acetate was added to the reaction solution, and the solution was washed twice with a saturate brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2) to obtain methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate as an oil (680 mg).

Workup

  1. stirringthe reaction solution was stirred at 60° C. for 12 hours
  2. washthe solution was washed twice with a saturate brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-ea4e4ed5c7ae4688b3f2b6f44c299427
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Reaction notes

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