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

HRID 2251179Notes

Reaction equation

HRID 2251179 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) and the precipitate
  6. customwas isolated by filtration
  7. washwashed several times with water

Sources & evidence

ORD record
ord-2198b4e6d33d45cf9a4817f95f586439
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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