Trifluoroacetic anhydride → 5-Chloro-2-fluoro-3-methoxybenzenethiol

Temperature

0 °C

To a mixture of 5-chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene (501 mg) and CH3CN (20 mL) was added TFAA (0.953 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The mixture was concentrated. The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C. The solution was stirred at 0° C. for 10 min, and concentrated in vacuo. The mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (303 mg).

1. waitat room temperature for 1 h
2. concentrationThe mixture was concentrated
3. dissolutionThe residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C
4. stirringThe solution was stirred at 0° C. for 10 min
5. concentrationconcentrated in vacuo
6. additionThe mixture was diluted with saturated aqueous NH4Cl
7. extractionextracted with EtOAc
8. extractionThe organic layer was extracted with 1N NaOH
9. extractionextracted with EtOAc
10. washThe organic layer was washed with brine
11. dry with materialdried over MgSO4
12. concentrationconcentrated in vacuo

ORD record

ord-af71b3f33a5d4dbf96c2ef2ed91e921f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2