Methanesulfonic Acid → Methyl 2-(4-chloro-7-fluoro-6-methoxy-1-benzothiophen-3-yl)acetate

HRID 591457Notes

Reaction equation

HRID 591457 reaction equation
S(O)(C)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([O:23][CH3:24])[C:10]([F:22])=[C:11]([S:13][CH2:14][C:15](=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=1>>[CH3:20][O:19][C:17](=[O:18])[CH2:16][C:15]1[C:12]2[C:7]([Cl:6])=[CH:8][C:9]([O:23][CH3:24])=[C:10]([F:22])[C:11]=2[S:13][CH:14]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 89767787Methyl 4-((5-chloro-2-fluoro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate

Product 1

HCID 121003826Methyl 2-(4-chloro-7-fluoro-6-methoxy-1-benzothiophen-3-yl)acetateYield 89.8%

Conditions

Temperature
0 °C

Procedure

MsOH (4.0 mL) was added to methyl 4-((5-chloro-2-fluoro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate (400 mg) at 0° C. After stirring at 0° C. for 20 min, the mixture was warmed to room temperature and stirred for 2 h. The mixture was poured into ice water at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (338 mg).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 2 h
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed successively with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-84b1bfb551484127aab4c47e31d72b3b
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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