methyl 4,5-dichloroisothiazole-3-carboxylate → HCID 66854171, compound

Add LiBH4 (2.0 M in THF, 10 mL, 20 mmol) to a solution of 4,5-dichloro-isothiazole-3-carboxylic acid methyl ester (2.1 g, 10 mmol) in THF (60 mL). Stir at room temperature for one hour and then cool to 0° C. Carefully quench the reaction mixture with water (10 mL), then saturated aqueous NH4Cl (50 mL). Extract into EtOAc (100 mL), then dry (MgSO4), filter, and concentrate the organics to give 540 mg crude product as an orange syrup. Purify the syrup on silica gel (40 g) using 5-30% EtOAc/hexanes to give 310 mg (17%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 5.55 (t, 1H, J=5.9 Hz), 4.52 (d, 2H, J=6.2 Hz).

1. temperaturecool to 0° C
2. customCarefully quench the reaction mixture with water (10 mL)
3. extractionExtract into EtOAc (100 mL)
4. dry with materialdry (MgSO4)
5. filtrationfilter
6. concentrationconcentrate the organics
7. customto give 540 mg crude product as an orange syrup
8. customPurify the syrup on silica gel (40 g)

ORD record

ord-90d0c79306b14fd49a117ed644bd1369

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968587B2