Methanethiol → 4-Chloro-3-(methylsulphenyl)-2-(methylsulphonyl)benzoic acid

HRID 341733Notes

Reaction equation

HRID 341733 reaction equation
O.[OH-].[Li+].[CH3:4][SH:5].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([S:16]([CH3:19])(=[O:18])=[O:17])[C:8]=1F.O>CN(C)C=O>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([S:16]([CH3:19])(=[O:18])=[O:17])[C:8]=1[S:5][CH3:4]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 544424304-Chloro-3-fluoro-2-methylsulphonylbenzoic acid

Product 1

HCID 536334514-Chloro-3-(methylsulphenyl)-2-(methylsulphonyl)benzoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium hydroxide monohydrate (1.26 g) was added to a solution of methyl mercaptan (0.72 g) in dimethyl formamide. To this mixture was added 4-chloro-3-fluoro-2-(methylsulphonyl)benzoic acid (3.7 g). The mixture was stirred for 2 hours then poured into water and acidified to pH1. It was extracted with ether, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with n-hexane and filtered to give 4-chloro-3-(methylsulphenyl)-2-(methylsulphonyl)benzoic acid (2.26 g) as a white solid, NMR (CDCl3) 2.5(s,3H), 3.45(s,3H), 7.5(d,1H), 7.7(d,1H).

Workup

  1. extractionIt was extracted with ether
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was triturated with n-hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4eb30192f8e248068641c6975323a920
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Reaction notes

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