Water → Methyl 3-(benzyloxy)-4,6-dibromopicolinate

HRID 584707Notes

Reaction equation

HRID 584707 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[OH:15].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 22175130Methyl 4,6-dibromo-3-hydroxypicolinate

Product 1

HCID 22175074Methyl 3-(benzyloxy)-4,6-dibromopicolinateYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of sodium hydride (0.6 g) in DMF (50 mL) was slowly added 14 (7.1 g). After the addition was complete, the mixture was stirred at room temperature for 15 minutes, then benzyl chloride (3.05 g) was added all at once. The mixture was then heated at 90° C. for six hours, cooled, poured into water (500 mL) and extracted with ether (2×200 mL). The ether extracts were combined, washed with 2N NaOH (50 mL), dried (MgSO4) and the solvent was evaporated to give 15 as a light yellow solid (8.3 g). Recrystallization from a small volume of methanol gave an analytical sample, m.p. 75-76° C.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was then heated at 90° C. for six hours
  3. temperaturecooled
  4. extractionextracted with ether (2×200 mL)
  5. washwashed with 2N NaOH (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4957b84dd0734ff1bdd648c1b40cd4e8
Source dataset
uspto-grants-2005_08
Patent number
US06927225B2

Reaction notes

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