Benzyl Bromide → Methyl 3-(benzyloxy)-6-bromopicolinate

HRID 2178255Notes

Reaction equation

HRID 2178255 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([OH:20])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:20][C:13]1[C:14]([C:16]([O:18][CH3:19])=[O:17])=[N:15][C:10]([Br:9])=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 59418684Methyl 3-(benzyloxy)-6-bromopicolinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl bromide (3.87 g, 22.6 mmol), was added to a suspension of methyl 6-bromo-3-hydroxypicolinate (5.00 g, 21.6 mmol) and K2CO3 (5.96 g, 43.1 mmol) in anhydrous DMF (40 mL). The reaction mixture was heated at 60° C. for 18 hours, cooled to rt, and poured into an ice/water mixture. After stirring for 2.5 hours, the precipitate was collected by filtration, washed with water, and dried to provide the desired product methyl 3-(benzyloxy)-6-bromopicolinate (29A).

Workup

  1. temperaturecooled to rt
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-89e605444477480ebbabc7aef63cc0ea
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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