Ethanol → (4-Fluoro-phenylsulfanyl)-acetic acid methyl ester

A solution of 4-fluorothiophenol (10 g, 78 mmol) in ethanol(200 mL) was treated with powdered KOH (9.6 g), stirred for 30 min at rt, then treated with a solution of bromoacetic acid (10.84 g, 78 mmol) in ethanol (50 mL) and stirred at 80 C for 4 h. the reaction was cooled to rt, partitioned between 1N HCl and EtOAc and the organics were washed with water, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in MeoH (250 mL), cooled to 0 C, treated with SOCl2 (8.5 mL) and stirred at rt overnight. The reaction was quenced with water, concentrated then partitioned between EtOAc (3 times) and water. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated to give 14.6 g of the title compound.

1. stirringstirred at 80 C for 4 h. the reaction
2. temperaturewas cooled to rt
3. custompartitioned between 1N HCl and EtOAc
4. washthe organics were washed with water
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe crude product was dissolved in MeoH (250 mL)
9. temperaturecooled to 0 C
10. additiontreated with SOCl2 (8.5 mL)
11. stirringstirred at rt overnight
12. concentrationconcentrated
13. customthen partitioned between EtOAc (3 times) and water
14. washThe combined organics were washed with brine
15. dry with materialdried (Na2SO4)
16. filtrationfiltered
17. concentrationconcentrated

ORD record

ord-ba0d6021697d40aba81f43691ed9f96c

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294573B1