Benzyl Bromide → 3-(Benzyloxy)-2-bromopyridine

HRID 1765067Notes

Reaction equation

HRID 1765067 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:9]([O:8][C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 107780003-(Benzyloxy)-2-bromopyridineYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-pyridine-3-ol (50.4 g, 0.29 mol), benzyl bromide (45.5 g, 0.28 mol) and potassium carbonate (52 g, 0.38 mol) in dry N,N-dimethylformamide (DMF; 300 mL) was heated at 110° C. for 30 minutes. The mixture was filtered through a pad of Celite®, the solvent was removed under reduced pressure and the black residue was taken up between ice cold 0.5 M aqueous NaOH and EtOAc. The organic phase was washed twice with brine, dried (MgSO4), and concentrated under reduced pressure to yield 69.6 g (93%) of the title compound as a brown oil. HRMS m/z calcd for C12H10BrNO (M)+ 263.9946. found 263.9939. *Previously described in J. Med. Chem. 1996, 39, 5267–5275.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. customthe solvent was removed under reduced pressure
  3. washThe organic phase was washed twice with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06e32383508c4278bfe889de86205fd4
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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