Dichloromethane → HCID 59280063, compound

The title compound was prepared by an adaptation of the method described in Robins, M. J. et al. (J. Am. Chem. Soc. 1983, 105, 4059-4065). 1-(2-Bromo-phenyl)-2,2,2-trifluoro-ethanol (615 mg, 2.41 mmol, as prepared in the previous step) was placed in an 8 mL vial equipped with a magnetic stir bar. DCM (4 mL) and TEA (1.2 eq., 0.403 mL, 2.89 mmol) were added via syringe. Phenyl chlorothionoformate (1.1 eq., 0.367 mL, 2.65 mmol) was added dropwise via syringe to the water-cooled solution. After completion of the addition, the reaction was stirred at RT for 16 h, poured into water, and extracted three times with DCM (10 mL). The combined organic extracts were dried over anhydrous MgSO4 filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using a 12-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 1:4, v/v over 30 min, yielding 695 mg (74%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.58-7.68 (m, 2H), 7.36-7.48 (m, 3H), 7.27-7.36 (m, 2H), 7.04-7.15 (m, 3H).

1. customThe title compound was prepared by an adaptation of the method
2. customvial equipped with a magnetic stir bar
3. temperaturecooled solution
4. additionAfter completion of the addition
5. extractionextracted three times with DCM (10 mL)
6. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customThe crude product was purified by column chromatography
10. washeluting with EtOAc/hexanes, 0:1 to 1:4, v/v over 30 min

ORD record

ord-1ed2facbac4a4e76ba0674a1dca65c98

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232409B2