Methanol → Benzoic acid, 4-fluoro-2-mercapto-, methyl ester

HRID 539948Notes

Reaction equation

HRID 539948 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([SH:11])[CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([SH:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 127373274-Fluoro-2-sulfanylbenzoic acid

Product 1

HCID 12737328Benzoic acid, 4-fluoro-2-mercapto-, methyl esterYield 70%

Procedure

A mixture of 4-fluoro-2-sulfanylbenzoic acid (6.0 g, 34.9 mmol), concentrated sulfuric acid (6 mL) in methanol (200 mL) was refluxed for 18 hours under argon atmosphere. The resulting mixture was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water, basified with a saturated aqueous solution of sodium bicarbonate to about pH 8. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 4.54 g of the crude product as a brown oil (yield was 70%), which was used directly for the next step without further purification. MS obsd. (ESI−) [(M−H)−] 185.

Workup

  1. temperaturewas refluxed for 18 hours under argon atmosphere
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f1615057dbe4e7c98097658df80ac49
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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