Ethanol → Ethyl 4-bromo-6-methylpicolinate

HRID 1908810Notes

Reaction equation

HRID 1908810 reaction equation
[K+].[Br:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([C:10]([O-:12])=[O:11])[CH:4]=1.[CH2:13](O)[CH3:14]>OS(O)(=O)=O.C([O-])(O)=O.[Na+]>[CH2:13]([O:11][C:10]([C:5]1[CH:4]=[C:3]([Br:2])[CH:8]=[C:7]([CH3:9])[N:6]=1)=[O:12])[CH3:14]

Participants

5

Reactant 2

HCID 702EthanolHCID 67027109HCID 67027109, compound

Product 1

HCID 25208981Ethyl 4-bromo-6-methylpicolinate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-bromo-6-methyl-pyridine-2-carboxylic acid potassium salt (253 mg, 0.996 mmol) in ethanol (100 mL), H2SO4 (2 mL) is added dropwise. The mixture is heated to 70° C. for 16 h before it is carefully diluted with sat. aq. NaHCO3. The mixture is extracted three times with diethyl ether. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates with heptane:EA 3:2 to give 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester (105 mg) as a pale yellow oil; LC-MS: tR=0.85 min, [M+1]+=244.22.

Workup

  1. additionis added dropwise
  2. extractionThe mixture is extracted three times with diethyl ether
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-206cfd363e164f28a5d5c20eddd7f3c9
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

Loading…