2,2,2,4'-Tetrafluoroacetophenone → 2,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

HRID 1917052Notes

Reaction equation

HRID 1917052 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:18])[CH:3]=1.C([Li])CCC.[F:24][C:25]([F:36])([F:35])[C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:27]>O1CCCC1>[F:36][C:25]([F:24])([F:35])[C:26]([C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)([C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:18])[CH:3]=1)[OH:27]

Participants

5

Reactant 3

HCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 594978222-(4-Bromo-2,6-dimethyl-phenyl)-1,1,1,3,3,3-hexamethyl-disilazaneHCID 178418339Butyllithium

Product 1

HCID 594978232,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane (Example II) (1.72 g, 5.0 mmol) in tetrahydrofuran (12 ml) under a nitrogen atmosphere was slowly added a solution of n-butyl lithium in hexanes (1.6 M) (3.3 ml, 5.28 mmol) at −70° C. The reaction mixture was stirred at −70° C. for 30 minutes before addition of 2,2,2,4′-tetrafluoroacetophenone (commercially available) (1.01 g, 5.25 mmol) at −70° C. The cooling bath was removed after 15 minutes. Once the reaction mixture had reached ambient temperature, it was poured onto water. The mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over sodium sulfate, and then concentrated. The title compound was isolated as a yellow oil.

Workup

  1. customThe cooling bath was removed after 15 minutes
  2. customhad reached ambient temperature
  3. additionit was poured onto water
  4. extractionThe mixture was extracted with diethyl ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fd90c40e3b4d43f995710731cd943f44
Source dataset
uspto-grants-2013_12
Patent number
US08618173B2

Reaction notes

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