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Hydrochloric Acid → 3-(Benzyloxy)-6-bromo-4-methoxypicolinic acid

HRID 1059659
Notes
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Reaction equation

HRID 1059659 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11]C)=[O:10])[C:3]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21](=O)([O-])[O-:22].[K+].[K+].CO.Cl>O>[Br:8][C:6]1[N:5]=[C:4]([C:9]([OH:11])=[O:10])[C:3]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:2]([O:22][CH3:21])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 22175074Methyl 3-(benzyloxy)-4,6-dibromopicolinate

Product 1

HCID 221750843-(Benzyloxy)-6-bromo-4-methoxypicolinic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A vigorously stirred mixture of 15 (25.5 g), potassium carbonate (75 g) and methanol (300 mL) was heated at reflux for 30 hours. The mixture was cooled, poured into water (800 mL), and the pH adjusted to 2 by the addition of conc. HCl. The resulting mixture was extracted with CH2Cl2 (3×150 mL). The organic extracts were combined, dried (MgSO4) and the solvent was evaporated to give a nearly colorless oil (20.5 g) which slowly solidified upon standing. This was recrystallized from methanol (125 mL)/water (40 mL) to give the desired acid 16 (11.6 g), m.p. 134-135° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 hours
  3. temperatureThe mixture was cooled
  4. extractionThe resulting mixture was extracted with CH2Cl2 (3×150 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d714a4837050406ab6c8121687c73e98
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521622B1

Reaction notes

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