Benzyl Bromide → 3-(Benzyloxy)-2,5-dibromopyridine

HRID 42167Notes

Reaction equation

HRID 42167 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O.O>[CH2:16]([O:8][C:7]1[C:2]([Br:1])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 467368242,5-Dibromopyridin-3-ol

Product 1

HCID 717109963-(Benzyloxy)-2,5-dibromopyridineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dibromopyridin-3-ol (200 mg, 0.791 mmol) in dry N,N-dimethylformamide (8 mL) was added potassium carbonate (164 mg, 1.19 mmol) and benzyl bromide (0.11 mL, 0.949 mmol). The mixture was stirred at room temperature for 2 hours, diluted with water (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1→3/2) to give the title compound as a white crystal (211 mg, yield 78%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1→3/2)

Sources & evidence

ORD record
ord-c8a0a158050e49dcaf45dfee4187d4a0
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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