(Trifluoromethyl)trimethylsilane → 1-(3,5-Bis-trifluoromethylphenyl)-2,2,2-trifluoro-1-(3-methyl-4-nitrophenyl)ethanol

HRID 1640101Notes

Reaction equation

HRID 1640101 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]([F:44])([F:43])[C:21]1[CH:22]=[C:23]([C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[C:34]([CH3:41])[CH:33]=2)[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1.[F:45][C:46]([Si](C)(C)C)([F:48])[F:47]>O1CCCC1.C(OCC)(=O)C>[F:19][C:20]([F:43])([F:44])[C:21]1[CH:22]=[C:23]([C:31]([C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[C:34]([CH3:41])[CH:33]=2)([OH:42])[C:46]([F:48])([F:47])[F:45])[CH:24]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:26]=1

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 219403763',5'-Bis-trifluoromethyl-3-methyl-4-nitrobenzophenone

Product 1

HCID 592295111-(3,5-Bis-trifluoromethylphenyl)-2,2,2-trifluoro-1-(3-methyl-4-nitrophenyl)ethanolYield 48.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (0.2 ml) was added to a solution of 3′,5′-bis-trifluoromethyl-3-methyl-4-nitrobenzophenone (1.4 g) and trifluoromethyltrimethyl-silane (1.0 g) in tetrahydrofuran (20 ml) in an ice bath and stirred at room temperature for 8 hours. The reaction solution was diluted with ethyl acetate and washed with water and a saturated salt solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was dissolved in tetrahydrofuran (20 ml) and, by adding 2N hydrochloric acid (2 ml), stirred at room temperature for 30 minutes. After diluting with ethyl acetate and washing with water and a saturated salt solution and after drying over anhydrous magnesium sulfate, the solvent was distilled off. Then the residue was purified by silica gel column chromatography to obtain 1-(3,5-bis-trifluoromethylphenyl)-2,2,2-trifluoro-1-(3-methyl-4-nitrophenyl)ethanol (0.8 g).

Workup

  1. washwashed with water
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in tetrahydrofuran (20 ml)
  5. additionby adding 2N hydrochloric acid (2 ml)
  6. stirringstirred at room temperature for 30 minutes
  7. additionAfter diluting with ethyl acetate
  8. washwashing with water
  9. dry with materiala saturated salt solution and after drying over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customThen the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-287ffb1fb65c4d6cb1c926df6d2c7054
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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