3-Bromo-1,1,1-Trifluoro-2-Propanol → HCID 87793684, compound

HRID 855223Notes

Reaction equation

HRID 855223 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].Br[CH2:26][CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29]>C(#N)C>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][N:10]([CH2:26][CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29])[C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 23665647Potassium tert-butoxideHCID 59344854HCID 59344854, compound

Product 1

HCID 87793684HCID 87793684, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

260 mg of N-(4-tert-butyl-benzyl)-2,2,2-trifluoro-acetamide (1 mmol) were dissolved in 10 ml acetonitrile and treated with 169 mg of potassium tert-butylate (1.5 mmol). After 5 min stirring at rt, 0.125 ml of [rac]-3-bromo-1,1,1-trifluoro-propan-2-ol (1.2 mmol) were added and the reaction mixture stirred at 75° C. bath temperature for 22 h. After cooling down to rt, the reaction mixture was concentrated in vacuo, dissolved in EtOAc/water and the phases separated. The organic phase was then washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:4) to give 111 mg of N-(4-tert-butyl-benzyl)-2,2,2-trifluoro-N-(3,3,3-trifluoro-2-hydroxy-propyl)-acetamide as a white solid (30%). MS (ISP) 301.2 (M+H)+.

Workup

  1. stirringthe reaction mixture stirred at 75° C. bath temperature for 22 h
  2. temperatureAfter cooling down to rt
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in EtOAc/water
  5. customthe phases separated
  6. washThe organic phase was then washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-2c2ba4a7d5e5439a813a868e8b1fd947
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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