Water → 5-(Benzyloxy)-2-bromopyridine

HRID 1966246Notes

Reaction equation

HRID 1966246 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.O>CN(C=O)C>[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 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 160946965-(Benzyloxy)-2-bromopyridineYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-hydroxypyridine (3 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 solution is stirred 24 hours. The reaction solution is pored into water and extracted with methyltert.-butyl ether. The combined organic layers are dried over Na2SO4 and the solvent is removed in vacuo. 5-Benzyloxy-2-bromo-pyridine is obtained after column chromatography as brown oil in a yield of 80%. HPLC (method C): 2.01 min; LC-MS (method A): 1.97 min, 264.00 (MH+).

Workup

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

Sources & evidence

ORD record
ord-d55dee8aef9f40309231d8959e1cc792
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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