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

HRID 1048940Notes

Reaction equation

HRID 1048940 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[O:3])[CH3:2].C[Si](C)(C)[C:13]([F:16])([F:15])[F:14].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O.ClCCl>[Br:10][C:8]1[CH:9]=[C:4]([C:1]([OH:3])([CH3:2])[C:13]([F:16])([F:15])[F:14])[CH:5]=[N:6][CH:7]=1

Participants

7

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 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3-acetyl-5-bromopyridine (0.20 g, 1.0 mmol) in tetrahydrofuran (3.3 mL) were added a solution of trimethyl(trifluoromethyl)silane in tetrahydrofuran (0.5 M, 4.0 mL, 2.0 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 0.1 mL, 0.1 mmol). The resulting reaction mixture was stirred at room temperature for 1 h, then diluted with water and dichloromethane. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0 to 6% dichloromethane in acetone) provided the title compound: LCMS m/z 271.75 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 1 H), 8.68 (s, 1 H), 8.11 (s, 1 H), 3.12 (br s, 1 H), 1.82 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (0 to 6% dichloromethane in acetone)

Sources & evidence

ORD record
ord-e2b99ea587024382803e02a8598255d5
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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