2-Bromopyridine → α-(2,5-Difluorophenyl)-2-pyridinemethanol

HRID 2080356Notes

Reaction equation

HRID 2080356 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]=[O:23]>O.O1CCCC1>[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]([OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8058HexaneHCID 1376632,5-DifluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23028683α-(2,5-Difluorophenyl)-2-pyridinemethanolYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A hexane solution (1.53M, 3.92 ml, 0.6 mmol) of n-butyl lithium was added dropwise to a tetrahydrofuran (10 ml) solution of 2-bromopyridine (572 μl, 6 mmol) under an argon atmosphere at −78° C., followed by stirring for 30 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (655 μl, 6 mmol) and the temperature of the reaction mixture was gradually raised to room temperature. To the reaction mixture was added water. The resulting mixture was then extracted with ethyl acetate. After the solvent was dried, the residue obtained by concentration under reduced pressure was purified by purification by silica gel chromatography to give the title compound (120 mg, 9%) as a white solid.

Workup

  1. extractionThe resulting mixture was then extracted with ethyl acetate
  2. customAfter the solvent was dried
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by purification by silica gel chromatography

Sources & evidence

ORD record
ord-fbd8e20c6b424698a5ea35cad2336c5f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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