Benzyl Bromide → 2-(Benzyloxy)-4-methylpyridine

HRID 1486237Notes

Reaction equation

HRID 1486237 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178428601HCID 178428601, compound

Product 1

HCID 142234762-(Benzyloxy)-4-methylpyridineYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13.6 ml (114 mmol, 1.0 eq.) of benzyl bromide and 15.0 g (137 mmol, 1.2 eq.) of 2-hydroxy-4-methylpyridine [CAS No: 13466-41-6] was dissolved in 470 ml of THF. The solution was admixed with 37.9 g (137 mmol, 1.2 eq.) of silver carbonate and the mixture was heated to reflux with exclusion of light overnight. Subsequently, the reaction mixture was filtered through kieselguhr and eluted with ethyl acetate, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5). 21.4 g of the title compound were obtained (94% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux with exclusion of light overnight
  3. filtrationSubsequently, the reaction mixture was filtered through kieselguhr
  4. washeluted with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-aa12926c7dfe431ebadb71396f925803
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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