Methanesulfonic Acid → Methyl(4,7-dichloro-6-methoxy-1-benzothiophen-3-yl)acetate

HRID 591429Notes

Reaction equation

HRID 591429 reaction equation
S(O)(C)(=O)=O.[Cl:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([Cl:15])=[CH:9][C:8]=1[S:16][CH2:17][C:18](=O)[CH2:19][C:20]([O:22][CH3:23])=[O:21]>>[CH3:23][O:22][C:20](=[O:21])[CH2:19][C:18]1[C:9]2[C:10]([Cl:15])=[CH:11][C:12]([O:13][CH3:14])=[C:7]([Cl:6])[C:8]=2[S:16][CH:17]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 89767715Methyl 4-((2,5-dichloro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate

Product 1

HCID 121003519Methyl(4,7-dichloro-6-methoxy-1-benzothiophen-3-yl)acetateYield 85%

Conditions

Temperature
0 °C

Procedure

MsOH (4.5 mL) was added to methyl 4-((2,5-dichloro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate (1.03 g) at 0° C. The mixture was stirred at 0° C. for 10 min and then at room temperature for 1.5 h. The mixture was poured into ice water 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 a solid. The solid was washed with hexane to give the title compound (0.827 g).

Workup

  1. waitat room temperature for 1.5 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
  8. customto give a solid
  9. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-f2f4d4bd6ba749c084b5011b2e91e806
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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