Bromine → HCID 86670331, compound

Participants

Reaction Steps

1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol (1.9 g, 5.8 mmol, published PCT patent application no. WO 2006/094842) was dissolved in acetic acid (10 mL). Bromine (1.9 g, 12 mmol) was added drop wise. The reaction was allowed to stir at room temperature until a solid precipitated. The solid was filtered, dissolved in EtOAc (100 mL) and washed with 1 N NaOH (3×50 mL). The organic layer was separated and washed with water (100 mL), brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue was dissolved in CH2Cl2 (20 mL). To this was added Hünig's base (1.0 mL) and 2-thiophenesulfonyl chloride (1.1 g, 5.8 mmol, Sigma-Aldrich, St. Louis, Mo.) at room temperature. After 3 h, the mixture was purified via column chromatography (40 g of silica, 10% EtOAc in hexanes) to afford 2-(3-bromo-4-(4-(thiophenylsulfonyl)piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (1.5 g).

Provenance & Evidence