Pyridine → 2-[(2-Bromophenyl)sulfanyl]acetic acid

2-Bromothiophenol (4.00 g, 21.6 mmol) was added to a solution of methyl 2-bromoacetate (2.20 mL, 23.3 mmol) and pyridine (1.88 mL, 23.3 mmol) in DMSO (50 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with EtOAc (300 mL) and the resulting solution was washed with water (2×250 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was dissolved in THF (50 mL), aqueous 1 N NaOH solution (25 mL, 25 mmol) was added and the mixture was stirred at room temperature for 45 min. The mixture was concentrated and the aqueous solution was diluted with aqueous 1 N NaOH solution. The solution was cooled to 0° C. and was slowly rendered acidic (pH=2) by addition of aqueous 1 N HCl solution. The resulting suspension was filtered, the solid was washed with water and dried under reduced pressure to give the title compound (3.71 g, 71% yield) as a white solid.

1. washthe resulting solution was washed with water (2×250 mL) and brine (100 mL)
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in THF (50 mL)
6. stirringthe mixture was stirred at room temperature for 45 min
7. concentrationThe mixture was concentrated
8. additionthe aqueous solution was diluted with aqueous 1 N NaOH solution
9. temperatureThe solution was cooled to 0° C.
10. additionby addition of aqueous 1 N HCl solution
11. filtrationThe resulting suspension was filtered
12. washthe solid was washed with water
13. customdried under reduced pressure

ORD record

ord-34d4357c38714672801af2b222803d1c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642277B2