Benzyl Bromide → HCID 57421820, compound

HRID 1496979Notes

Reaction equation

HRID 1496979 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 57421820HCID 57421820, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-hydroxynicotinate (8.5 g, 55.6 mmol) and K2CO3 (11.5 g, 83.3 mmol) in DMF (20 mL) at 0° C. was added (bromomethyl)benzene (8 mL, 66.7 mmol) drop wise over 5 min. The resulting mixture was stirred at room temperature for 2 hours. The mixture was quenched with water (100 mL) and extracted with EA (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1) to give methyl 5-(benzyloxy)nicotinate (4 g, 30.7%) as a yellow oil.

Workup

  1. customThe mixture was quenched with water (100 mL)
  2. extractionextracted with EA (100 mL×3)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with petroleum ether/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-ef47ce5b56f8412fa8aa3c361f8c1ddd
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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