Benzyl Bromide → 5-(Benzyloxy)-2-chloropyridine

HRID 1864751Notes

Reaction equation

HRID 1864751 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][N:5]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC.CN(C=O)C.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][N:5]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 100137175-(Benzyloxy)-2-chloropyridineYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (55% in oil, 236 mg, 5.40 mmol) washed in Hexane and 2-Chloro-5-hydroxypyridine (350 mg, 2.70 mmol) was suspended in dry DMF (20 ml). After 10 minutes at room temperature Benzylbromide (0.32 ml, 2.70 mmol) was added and the mixture was stirred for an additional 2 hrs. The reaction was diluted with water and extracted with EtOAc (3*50 ml). The combined organic layers were washed with water and brine, and dried over Na2SO4. The solvent was removed by rotary evaporation, affording 520 mg (88%) of the title compound as a yellow oil.

Workup

  1. extractionextracted with EtOAc (3*50 ml)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-eb8e7ef0e5e74c9d96b2013f5d58790d
Source dataset
uspto-grants-2009_12
Patent number
US07625934B2

Reaction notes

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