Ethanol → Ethyl 6-Bromopicolinate

HRID 741817Notes

Reaction equation

HRID 741817 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11][CH2:12]N(CC)CC.ClC(OCC)=O.CCO>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 2758810Ethyl 6-Bromopicolinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-bromopicolinic acid from Step 1 (92 g, 0.455 mol) and Et3N (69 g, 0.68 mol) in THF (1.1 L) at 0° C. there was slowly added ethyl chloroformate (61.6 g, 0.57 mol). The resulting suspension was stirred at 0° C. for 15 min., EtOH (250 mL) was added, and the mixture was stirred at r.t. overnight. After filtration, the filtrate was evaporated down, the residue was taken up in ET2O (1 L) and filtered again. The filtrate on evaporation of the solvents afforded the title compound as an oil which was immediately used as such.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at r.t. overnight
  3. filtrationAfter filtration
  4. customthe filtrate was evaporated down
  5. filtrationfiltered again
  6. customThe filtrate on evaporation of the solvents

Sources & evidence

ORD record
ord-28122d0446874fd08673a0c07d862d01
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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