Dimethylformamide → HCID 57930975, compound

HRID 1096983Notes

Reaction equation

HRID 1096983 reaction equation
CI.CN([CH:6]=[O:7])C.[Br:8][C:9]1[C:18]([O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Br:8][C:9]1[C:18]([O:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:21])=[O:22])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:7][CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57930950HCID 57930950, compound

Product 1

HCID 57930975HCID 57930975, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1-liter egg plant-type flask, methyl iodide (6.67 mL, 105 mmol) was added to a DMF (200 mL) solution of methyl 4-bromo-3-hydroxy-5-{[(trifluoromethyl)sulfonyl]oxy}benzoate (19.9 g) and potassium carbonate (14.5 g, 105 mmol), and stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline water, dried with sodium sulfate, filtered, and concentrated to obtain a crude product. This was purified through silica gel column chromatography (Biotage [SiO2, 40+M]) with a hexane/ethyl acetate developer system to obtain the title compound as a colorless solid.

Workup

  1. washwashed with water and saturated saline water
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThis was purified through silica gel column chromatography (Biotage [SiO2, 40+M]) with a hexane/ethyl acetate developer system

Sources & evidence

ORD record
ord-617ec381930845d4b4e6d0902a3af46e
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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