Dimethylformamide → 2-(4-Bromo-benzyloxy)-3-fluoro-pyridine

HRID 640430Notes

Reaction equation

HRID 640430 reaction equation
CN(C)C=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.[H-].[Na+].Cl[C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][N:19]=1>O>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 592552352-(4-Bromo-benzyloxy)-3-fluoro-pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (15 mL) solution of (4-bromo-phenyl)-methanol (1.56 g, 8.34 mmol) was added sodium hydride (401 mg, 8.35 mmol, 50% in oil), which was stirred for 5 minutes at room temperature. Then, an N,N-dimethylformamide (5 mL) solution of 2-chloro-3-fluoropyridine (967 mg, 7.35 mmol) was added to this mixture, which was stirred for 1 hour and 10 minutes at room temperature. Water was to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (2.03 g, 98%).

Workup

  1. stirringwas stirred for 1 hour and 10 minutes at room temperature
  2. customwas to the reaction mixture at room temperature
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b8d419e0114044c6960c12f2d51b4d5b
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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