Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

HRID 2254153Notes

Reaction equation

HRID 2254153 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16](Br)[CH:17]=1>CN(C)C=O>[CH2:3]([O:10][C:16]1[CH:17]=[C:12]([Br:11])[CH:13]=[N:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Product 1

HCID 153891983-(Benzyloxy)-5-bromopyridineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (50% w/w dispersion in mineral oil, 5 g) was added portionwise to a mixture of benzyl alcohol (12.4 g) and dimethylformamide (150 ml) which had been cooled to 0° C. The mixture was allowed to warm to ambient temperature and was stirred for 1 hour. 3,5-Dibromopyridine (25.2 g) was added and the mixture was heated to 60° C. for 2 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and a dilute aqueous potassium carbonate solution. The organic layer was washed with a dilute aqueous hydrochloric acid solution and with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was a red oil which on trituration under petroleum ether (b.p. 60°-80° C.) gave 5-benzyloxy-3-bromopyridine (18.6 g, 67%), m.p. 65°-67° C.

Workup

  1. temperatureto warm to ambient temperature
  2. temperaturethe mixture was heated to 60° C. for 2 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. custompartitioned between ethyl acetate
  5. washThe organic layer was washed with a dilute aqueous hydrochloric acid solution and with a saturated aqueous sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-85e4433f17494431aed0cef87e0e9259
Source dataset
uspto-grants-1993_08
Patent number
US05234950

Reaction notes

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