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

HRID 1966210Notes

Reaction equation

HRID 1966210 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C.O>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[N:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 160946965-(Benzyloxy)-2-bromopyridineYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

11.1 2-Bromo-5-hydroxypyridine (2 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min, benzylbromide (1.1 eq.) is added and the reaction stirred 16 h at RT. The reaction solution is diluted with water and extracted with methyl tert.-butyl ether. The combined organic layers are dried over Na2SO4 and the solvent removed in vacuo. 5-Benzyloxy-2-bromo-pyridine is obtained after column chromatography (heptan/ethyl acetate) as a colourless powder in a yield of 64%; HPLC (method C): 2.09 min; LC-MS (method A): 1.987 min, 263.95 (M+H+).

Workup

  1. extractionextracted with methyl tert.-butyl ether
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c800c46e18a24681ab346cff37e92d7f
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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