Methyl iodide → 5-Methanesulfonyl-2-trifluoromethoxy-benzoic acid

HRID 1820724Notes

Reaction equation

HRID 1820724 reaction equation
[S:1]([C:4]1[CH:5]=[CH:6][C:7]([O:13][C:14]([F:17])([F:16])[F:15])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([OH:3])=[O:2].[C:18](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:18][S:1]([C:4]1[CH:5]=[CH:6][C:7]([O:13][C:14]([F:15])([F:16])[F:17])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69037717Benzoic acid, 5-sulfino-2-(trifluoromethoxy)-

Product 1

HCID 690390475-Methanesulfonyl-2-trifluoromethoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-Sulfino-2-trifluoromethoxy-benzoic acid (0.82 g) in DMF (5 mL) was added 1.3 g of potassium carbonate, and the reaction mixture was stirred for 5 minutes before methyl iodide (0.66 mL) was added. The reaction mixture was then stirred at room temperature for 60 hours. After such time the reaction mixture was concentrated in vacuo, and the residue was treated with 1N NaOH (10 mL) and THF (4 mL). The reaction mixture was stirred for a further 2 hours at room temperature. After such time the solution was acidified with concentrated HCl solution. THF was then removed in vacuo, and the precipitate was isolated by filtration and washed several times with water to yield the title compound. MS (m/e): 283.0 (M−H, 100%).

Workup

  1. additionwas added
  2. concentrationAfter such time the reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with 1N NaOH (10 mL) and THF (4 mL)
  4. stirringThe reaction mixture was stirred for a further 2 hours at room temperature
  5. customTHF was then removed in vacuo
  6. customthe precipitate was isolated by filtration
  7. washwashed several times with water

Sources & evidence

ORD record
ord-2ab9849ee1944bb397993fe1b539e700
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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