Water → Methyl 3-(benzyloxy)-6-bromopicolinate

HRID 2201514Notes

Reaction equation

HRID 2201514 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[CH2:19]([O:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 59418684Methyl 3-(benzyloxy)-6-bromopicolinateYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-bromo-3-hydroxypicolinate (500 mg, 2.15 mmol), BnBr (443 mg, 3.25 mmol) and K2CO3 (595 mg, 4.31 mmol) in THF (5 mL) was stirred at RT for 3 h. Then water was added and the mixture was extracted with EtOAc (20 mL*3). The organic layer was dried over Na2SO4 and concentrated to give crude methyl 3-(benzyloxy)-6-bromopicolinate (500 mg, yield 72%), which was used for the next step without further purification. MS (M+H)+: 322/324.

Workup

  1. extractionthe mixture was extracted with EtOAc (20 mL*3)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a7eec012fba54c9fa08dfe2ac6e553f3
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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