Hydrochloric Acid → Benzoic acid, 3-mercapto-5-(trifluoromethyl)-, methyl ester

To a solution of 3-trifluoromethyl-5-(2-trimethylsilanyl-ethylsulfanyl)-benzoic acid methyl ester (580 mg, 1.72 mmol) in tetrahydrofuran (15 mL) was added tetrabutylammonium fluoride (1M solution in tetrahydrofuran, 11.6 mL, 11.6 mmol) and the yellow solution was stirred at room temperature for 1 hour. The reaction mixture was poured on aqueous 1M hydrochloric acid (30 mL) and ethyl acetate (30 mL) and the layers were separated. The aqueous layer was extracted a second time with ethyl acetate (30 mL). The organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Yellow solid (295 mg, 72%). MS (ESI−): m/z=235.01 ([M−H]−).

1. customthe layers were separated
2. extractionThe aqueous layer was extracted a second time with ethyl acetate (30 mL)
3. washThe organic layers were washed with 30 mL brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe compound was purified by silica gel chromatography on a 20 g column
8. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

ORD record

ord-9cf5e834fe564b0ebf2c780a74cdcc58

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748434B2