Benzyl Bromide → HCID 117600053, compound

HRID 1746449Notes

Reaction equation

HRID 1746449 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178497975HCID 178497975, compound

Product 1

HCID 117600053HCID 117600053, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 6-hydroxypicolinate (3.06 g, 20.0 mmol), (bromomethyl)benzene (6.84 g, 40.0 mmol), and silver carbonate (11 g, 40 mmol) in toluene (150 mL) was stirred at 80° C. overnight. After cooling and filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to give methyl 6-(benzyloxy)picolinate (2.6 g, 53%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with petroleum ether/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-093f203050344805990b9c6d8130dd4b
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

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