Benzyl Bromide → HCID 117600053, compound

HRID 1496975Notes

Reaction equation

HRID 1496975 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-90c5d139e45f4355a183a5108fb3e4fe
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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