(Trifluoromethyl)trimethylsilane → 1-(5-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-ol

HRID 712713Notes

Reaction equation

HRID 712713 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[CH:5]=[N:6][CH:7]=1.C[Si](C)(C)[C:12]([F:15])([F:14])[F:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:9])[C:12]([F:15])([F:14])[F:13])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 667978811-(5-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-olYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of 5-bromo-pyridine-3-carbaldehyde (2.0 g, 10.8 mmol) in THF (25 mL) are added trimethyl-trifluoromethyl-silane (2.8 mL, 18.8 mmol) and TBAF in THF solution (1.0 M; 10.8 mL, 10.8 mmol). The mixture is warmed to room temperature for 3 hrs. The solvent is evaporated to give the crude product. Purification by flash column chromatography affords 1.9 g of 1-(5-bromo-pyridin-3-yl)-2,2,2-trifluoro-ethanol.

Workup

  1. customThe solvent is evaporated
  2. customto give the crude product
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-e3606978dc91405b850b853058c74d50
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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