Hydrochloric Acid → Methyl 6-bromo-3-chloropicolinate

HRID 1852373Notes

Reaction equation

HRID 1852373 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([Cl:11])=[CH:4][CH:3]=1.Cl.[CH3:13]O>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[C:5]([Cl:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887Methanol2×HCID 534102656-Bromo-3-chloropicolinic acid

Product 1

HCID 21696654Methyl 6-bromo-3-chloropicolinate

Procedure

8.12 g (34.3 mmol) of 6-bromo-3-chloropyridine-2-carboxylic acid are admixed with 50 ml (1.25M; 62.5 mmol) of a solution of hydrogen chloride in methanol. The mixture is heated under reflux for 2 h, in the course of which 20 ml each time (1.25M; 25 mmol) of a solution of hydrogen chloride in methanol are added every 30 min. For workup, the reaction mixture is freed of the solvent on a rotary evaporator and the residue is admixed with diethyl ether and an aqueous sodium hydrogencarbonate solution. After the phase separation, the organic phase is dried; after the filtration, the filtrate is freed of the solvent on a rotary evaporator. The residue obtained is 7.78 g of the product with a purity of approx. 90% by weight.

Workup

  1. temperatureThe mixture is heated
  2. additionare added every 30 min
  3. customFor workup, the reaction mixture is freed of the solvent on a rotary evaporator
  4. customAfter the phase separation
  5. customthe organic phase is dried
  6. filtrationafter the filtration
  7. customthe filtrate is freed of the solvent on a rotary evaporator
  8. customThe residue obtained

Sources & evidence

ORD record
ord-90b92922420041bda995da149ba1cd17
Source dataset
uspto-grants-2015_02
Patent number
US08962529B2

Reaction notes

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