Benzyl Alcohol → 2-Benzyloxy-5-bromopyridine

HRID 747151Notes

Reaction equation

HRID 747151 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1>CN(C)C=O.[Cl-].[NH4+]>[CH2:1]([O:8][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 111081912-Benzyloxy-5-bromopyridineYield 106.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of benzyl alcohol (11.4 g, 0.105 mol) in N,N-dimethylformamide (250 ml) was added 70% oily sodium hydride (4.2 g, 0.123 mol) at 0° C., followed by stirring as it was for 1.5 hours. Then, 2,5-dibromopyridine (25 g, 0.106 mol) was added thereto, followed by stirring at 70° C. for 2 hours. After cooling as it was, the reaction mixture was diluted with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with a saturated aqueous ammonium chloride solution twice, dried over anhydrous magnesium sulfate and concentrated, to give a crude product of the title compound (29.5 g) as a pale yellow liquid.

Workup

  1. stirringby stirring at 70° C. for 2 hours
  2. temperatureAfter cooling as it
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with a saturated aqueous ammonium chloride solution twice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4ede701cf0941fa83bca4b3717d065b
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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