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

HRID 591445Notes

Reaction equation

HRID 591445 reaction equation
S(O)(C)(=O)=O.[F:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[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]([CH3:15])=[CH:11][C:12]([O:13][CH3:14])=[C:7]([F:6])[C:8]=2[S:16][CH:17]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 89767691Methyl 4-((2-fluoro-3-methoxy-5-methylphenyl)sulfanyl)-3-oxobutanoate

Product 1

HCID 121004334Methyl(7-fluoro-6-methoxy-4-methyl-1-benzothiophen-3-yl)acetateYield 96.7%

Conditions

Temperature
0 °C

Procedure

MsOH (3.0 mL) was added to methyl 4-((2-fluoro-3-methoxy-5-methylphenyl)sulfanyl)-3-oxobutanoate (330 mg) at 0° C. After stirring at 0° C. for 10 min, 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 (299 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-789bd90cd1ab4c93935abce7daa84cf8
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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