Benzyl Bromide → 2-Benzyloxy-3-bromopyridine

HRID 860730Notes

Reaction equation

HRID 860730 reaction equation
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([O:8][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178517701HCID 178517701, compound

Product 1

HCID 147124562-Benzyloxy-3-bromopyridineYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-bromo-2-hydroxypyridine (1.74 g, 10 mmol) was added to a suspension of NaH (440 mg of 60% dispersion in mineral oil, 11 mmol) in DMF (10 mL), and the resultant mixture was stirred at rt for 30 min. Benzyl bromide (1.3 mL, 11 mmol) was then added, and the reaction was stirred at rt overnight. It was then quenched by the addition of water, and the product extracted with ethyl acetate (2×50 mL). The extracts were combined, washed with 1N HCl solution, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography using hexanes to 100% ethyl acetate in hexanes as eluent to give the title compound as a colorless thick oil, (1.37 g, 52% yield). MS m/z 264, 266(MH+); 1H NMR (500 MHz, CDCl3) δ ppm 5.17 (s, 2 H) 6.05 (t, J=7.02 Hz, 1 H) 7.27–7.88 (m, 6 H) 7.70 (dd, J=7.17, 1.98 Hz, 1 H)

Workup

  1. customIt was then quenched by the addition of water
  2. extractionthe product extracted with ethyl acetate (2×50 mL)
  3. washwashed with 1N HCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-85f39ec7d4c1498ca9f8e435b0b88414
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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