Methanol → Methyl 3-bromo-6-chloropicolinate

HRID 2208803Notes

Reaction equation

HRID 2208803 reaction equation
[Br:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:17]O>>[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:17])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 269667323-Bromo-6-chloropyridine-2-carboxylic acid

Product 1

HCID 46311200Methyl 3-bromo-6-chloropicolinateYield 93%

Procedure

To a stirred solution of 3-bromo-6-chloropyridine-2-carboxylic acid (2.00 g, 8.46 mmol) in MeOH (40 ml) was added H2SO4 (189 μl, 3.55 mmol) and the solution was heated to reflux for 16 h. The reaction was cooled and the MeOH removed under reduced pressure, the resulting solid was dissolved in EtOAc (100 ml) and washed with saturated NaHCO3 solution (2×50 ml) followed by brine (50 ml), dried (Na2SO4) and evaporated under reduced pressure to afford the title compound as an off-white solid (1.97 g, 93%) which was used without any further purification. LC-MS 98%, m/z=249.8/251.7/253.7

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction was cooled
  4. customthe MeOH removed under reduced pressure
  5. dissolutionthe resulting solid was dissolved in EtOAc (100 ml)
  6. washwashed with saturated NaHCO3 solution (2×50 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-079fa3a6aacc450da6aa46cf1b2f89a7
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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