Bromine → HCID 86670331, compound

HRID 1972437Notes

Reaction equation

HRID 1972437 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[Br:23]Br.CCN(C(C)C)C(C)C.[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[S:39](Cl)(=[O:41])=[O:40]>C(O)(=O)C>[Br:23][C:13]1[CH:14]=[C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:21])[F:22])[CH:10]=[CH:11][C:12]=1[N:15]1[CH2:20][CH2:19][N:18]([S:39]([C:35]2[S:34][CH:38]=[CH:37][CH:36]=2)(=[O:41])=[O:40])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 24408BromineHCID 81531DiisopropylethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 866237611,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 86670331HCID 86670331, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. customprecipitated
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in EtOAc (100 mL)
  4. washwashed with 1 N NaOH (3×50 mL)
  5. customThe organic layer was separated
  6. washwashed with water (100 mL), brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  11. customthe mixture was purified via column chromatography (40 g of silica, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-85fa5ad261e740caa9fb2d5d716efb2c
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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