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

HRID 591446Notes

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]

Participants

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

temperatureAfter cooling
extractionextracted with EtOAc
washThe organic layer was washed successively with water and brine
dry with materialdried over MgSO4
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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