Bromine → HCID 86670387, compound

HRID 1972530Notes

Reaction equation

HRID 1972530 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]1

Participants

5

Reactant 2

HCID 24408BromineHCID 86670385HCID 86670385, compound

Product 1

HCID 86670387HCID 86670387, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24477Sodium ThiosulfateSolvent

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.

Workup

  1. extractionextracted with EtOAc (15 mL)
  2. customThe organic layer was separated
  3. washwashed with water (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was absorbed onto a plug of silica gel
  8. custompurified by column chromatography (12 g of silica gel, 10 to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7dc565108f4c4bc392aa59dbb0188c98
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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