Methyl iodide → 2-Chloro-5-(methylsulphonyl)benzoic acid

HRID 1723639Notes

Reaction equation

HRID 1723639 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([OH:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].[CH3:16]I>CO.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:16])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium Hydroxide2×HCID 151129042-Chloro-5-sulfino-benzoic acid

Product 1

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g (4 mmol) 2-Chloro-5-sulfino-benzoic acid in 20 ml methanol and 20 ml water was treated with 10N NaOH to pH=9 before adding 1.7 g (12 mmol) methyliodide. The mixture was heated for 48 h to 80° C. with occasional addition of NaOH to maintain pH=9. After removal of all volatiles HCl conc. was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried with MgSO4 and evaporated to dryness. The residue was taken up in methanol and subjected to reversed phase HPLC purification eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 323 mg (34%) of the title compound. MS (m/e): 233.0 (M−H, 100%)

Workup

  1. temperatureto maintain pH=9
  2. customAfter removal of all volatiles HCl conc.
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. customevaporated to dryness
  7. customsubjected to reversed phase HPLC purification
  8. washeluting with an acetonitrile/water gradient
  9. customto yield
  10. customafter evaporation of the product fractions 323 mg (34%) of the title compound

Sources & evidence

ORD record
ord-9c18e0ca33194af689794e622c9f4963
Source dataset
uspto-grants-2009_02
Patent number
US07485637B2

Reaction notes

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