Trifluoroacetic anhydride → 2-Fluoro-3-methoxy-5-methylbenzenethiol

Temperature

0 °C

To a mixture of 2-fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene (486 mg) and CH3CN (20 mL) was added TFAA (1.02 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, and concentrated in vacuo. 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 room temperature for 1 h, and concentrated in vacuo. The residue was diluted with saturated aqueous NH4Cl, and the mixture was extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (214 mg).

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

ORD record

ord-ea7f7ee883d241b3b60d95f0f3c2670a

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2