Ethanol → Ethyl 6-Bromopicolinate

HRID 853775Notes

Reaction equation

HRID 853775 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:15][CH3:16])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 2758810Ethyl 6-Bromopicolinate

Conditions

Temperature
25 °C

Procedure

To a stirring solution of 6-bromopicolinic acid (14.25 g, 70.3 mmol) in anhydrous ethanol (250 ml) was slowly added thionyl chloride (60 ml) at 5° C. After the addition was completed, the ice-bath was removed and the mixture was stirred at 25° C. for 3 hr. The solvent was evaporated under vacuum, the aqueous residue basified with saturated sodium carbonate, and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated to give ethyl 6-bromopicolinate as a white solid (15.75 g).

Workup

  1. customat 5° C
  2. additionAfter the addition
  3. customthe ice-bath was removed
  4. customThe solvent was evaporated under vacuum
  5. extractionextracted with DCM
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aa62853bbc714a6486b96cafb82ff005
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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