Benzyl Alcohol → 2-Benzyloxy-6-bromopyridine

HRID 356823

Reaction equation

HRID 356823 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=1>CN(C)C=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

Product 1

HCID 8174752-Benzyloxy-6-bromopyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.9 ml benzyl alcohol was dissolved in 10 ml N,N-dimethylformamide and 0.7 g sodium hydride (purity 95%) was slowly added. After gas evolution has ceased, 6 g 2,6-dibromopyridine was added and the mixture heated to reflux for 3 hours. After cooling, the reaction mixture was filtered through a silica gel column using hexane/ethyl acetate 1/1. The solvent was removed in vacuo and the crude product purified by flash silica gel column chromatography. The title compound was obtained as a colourless oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through a silica gel column
  5. customThe solvent was removed in vacuo
  6. customthe crude product purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-dd8a0f9c73de4234a94252a5f2a542a8
Source dataset
uspto-grants-1998_11
Patent number
US05840654

Linked notes

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