3,5-Bis(trifluoromethyl)benzyl bromide → HCID 22353131, compound

HRID 895338Notes

Reaction equation

HRID 895338 reaction equation
[C:1]1([CH:7]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)[CH2:8][S:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[F:32][C:33]([F:47])([F:46])[C:34]1[CH:35]=C([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)CBr>CO>[F:32][C:33]([F:46])([F:47])[C:34]1[CH:35]=[C:11]([CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=1)[CH2:10][S:9][CH2:8][CH:7]([N:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 10942334Sodium MethoxideHCID 86590283HCID 86590283, compound

Product 1

HCID 22353131HCID 22353131, compoundYield 114.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask fitted with a reflux condenser and a thermometer 2.76 g (6.6 mmoles) of thioacetate 83 and 250 ml of degassed methyl alcohol are introduced. The mixture is cooled to 0° C. and 356 mg (6.6 mmoles) of sodium methylate are added. The mixture is stirred under argon for one hour at 0° C., and 1.9 g (7.26 mmoles) of 3,5-bis-trifluoromethyl-benzyl bromide are added. The mixture is stirred for 48 hours, volatile substances are removed under reduced pressure, and 100 ml of water are added. The aqueous phase is extracted three times with methylene chloride, the combined organic phases are washed with brine and dried over magnesium sulfate. Volatile substances are removed under reduced pressure, affording 4.54 g of crude 1-[2-(3,5-bis-trifluoromethyl-benzylsulfanyl)-1-phenyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine (compound 84) as a colorless oil. This oil was purified by chromatography on silica gel (eluent: methylene chloride-hexane 65/35 (v/v)), affording 3.26 g of compound 84 as a colorless oil. Yield: 82%.

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. stirringThe mixture is stirred for 48 hours
  3. customvolatile substances are removed under reduced pressure, and 100 ml of water
  4. additionare added
  5. extractionThe aqueous phase is extracted three times with methylene chloride
  6. washthe combined organic phases are washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customVolatile substances are removed under reduced pressure

Sources & evidence

ORD record
ord-4c578c98930949cd80a6a54e08f51ff8
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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