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

HRID 2207343Notes

Reaction equation

HRID 2207343 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[N:24][CH:25]=1.C[Si](C)(C)[C:31]([F:34])([F:33])[F:32]>C1COCC1.O>[Br:19][C:20]1[CH:21]=[C:22]([C:26]([OH:28])([CH3:27])[C:31]([F:34])([F:33])[F:32])[CH:23]=[N:24][CH:25]=1

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 8204233-Acetyl-5-bromopyridineHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 666852642-(5-Bromopyridin-3-yl)-1,1,1-trifluoropropan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 33 μl, 0.033 mmol) was added to a solution of 1-(5-bromopyridin-3-yl)ethanone (65 mg, 0.33 mmol) and trimethyl(trifluoromethyl)silane (92 mg, 0.65 mmol) in THF (1.1 mL) at ambient temperature. After 30 minutes, the reaction mixture was diluted with water and extracted with DCM, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-30% ethyl acetate/hexanes, linear gradient) to afford 2-(5-bromopyridin-3-yl)-1,1,1-trifluoropropan-2-ol. MS ESI calc'd. for C8H8BrF3NO [M+H]+ 270 and 272. found 270 and 272. 1H NMR (500 MHz, CDCl3) δ 8.72 (s, 1H), 8.69 (d, J=2.5 Hz, 1H), 8.10-8.08 (m, 1H), 2.58 (s, 1H), 1.82 (s, 3H).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-30% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-5a1e68a1305a4044960d86a366cefd15
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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