Bromine → HCID 86670387, compound
Reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[Br:32]Br>CCO.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:32][C:11]1[CH:10]=[C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:30])[F:31])[CH:14]=[CH:13][C:12]=1[N:15]1[CH2:16][CH2:17][CH:18]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:19][CH2:20]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1,1,1,3,3,3-hexafluoro-2-(4-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)-2-propanol (699 mg, 1.49 mmol) in EtOH (10 mL) was added bromine (77 μL, 1.49 mmol) and the reaction mixture was stirred at room temperature for 15 min. The reaction mixture was diluted with a saturated aqueous sodium thiosulfate (10 mL) and extracted with EtOAc (15 mL). The organic layer was separated and washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (12 g of silica gel, 10 to 25% EtOAc in hexanes) to provide 2-(3-bromo-4-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (567 mg) as a mixture of two enantiomers.