Dimethylformamide → Methyl 2-(4-chloro-7-fluoro-6-hydroxy-1-benzothiophen-3-yl)acetate

Temperature

160 °C

To a mixture of methyl(4-chloro-7-fluoro-6-methoxy-1-benzothiophen-3-yl)acetate (284.8 mg) and DMF (dry) (8.0 mL) was added sodium 2-methyl-2-propanethiolate (443 mg). The mixture was stirred at 160° C. for 45 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, filtered and concentrated in vacuo. The residue was dissolved in MeOH (6.0 mL). To the solution was added conc. H2SO4 (0.100 mL). The mixture was stirred at 70° C. for 1 h. The mixture was concentrated. The residue was neutralized with saturated aqueous NaHCO3, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residual solid was washed with toluene and hexane to give the title compound (229.3 mg).

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. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in MeOH (6.0 mL)
8. additionTo the solution was added conc. H2SO4 (0.100 mL)
9. stirringThe mixture was stirred at 70° C. for 1 h
10. concentrationThe mixture was concentrated
11. extractionthe mixture was extracted with EtOAc
12. washThe combined organic layer was washed with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. washThe residual solid was washed with toluene and hexane

ORD record

ord-3d4b652f45da49e68815334fcb9f8e50

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2