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Dimethylformamide → (7-Fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetic acid

HRID 591446
Notes
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Reaction equation

HRID 591446 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[C:9]2[C:10]([CH3:17])=[CH:11][C:12]([O:15]C)=[C:13]([F:14])[C:8]=2[S:7][CH:6]=1.CN(C=O)C.CC([S-])(C)C.[Na+]>O.Cl>[F:14][C:13]1[C:8]2[S:7][CH:6]=[C:5]([CH2:4][C:3]([OH:18])=[O:2])[C:9]=2[C:10]([CH3:17])=[CH:11][C:12]=1[OH:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 5147913Sodium 2-methyl-2-propanethiolateHCID 121004334Methyl(7-fluoro-6-methoxy-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767685(7-Fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetic acidYield 122.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric Acid
Solvent
HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of methyl(7-fluoro-6-methoxy-4-methyl-1-benzothiophen-3-yl)acetate (248.4 mg) and DMF (dry) (7.5 mL) was added sodium 2-methyl-2-propanethiolate (415 mg) at room temperature. The mixture was stirred at 160° C. for 20 min. After cooling, the mixture was diluted with water and 1N HCl and extracted with EtOAc. The organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo to give the title compound (273 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e10a423cf2447e088542f84347477cd
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238639B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes