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

HRID 748736Notes

Reaction equation

HRID 748736 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-pyridinemethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customAfter drying the solvent
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by silica gel chromatography, whereby the title compound (120 mg, 9%)
  5. customwas obtained as a white solid

Sources & evidence

ORD record
ord-68bbf5d4e96642e1b55ea642ce0f81bb
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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