Ethanol → Ethyl 5-bromo-4-methylpicolinate

HRID 1908798Notes

Reaction equation

HRID 1908798 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.C([O-])(O)=O.[Na+].[CH2:17](O)[CH3:18]>OS(O)(=O)=O>[CH2:17]([O:9][C:8]([C:5]1[CH:4]=[C:3]([CH3:11])[C:2]([Br:1])=[CH:7][N:6]=1)=[O:10])[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 457900315-Bromo-4-methylpyridine-2-carboxylic acid

Product 1

HCID 66933529Ethyl 5-bromo-4-methylpicolinate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of crude 5-bromo-4-methyl-pyridine-2-carboxylic acid (10.9 g, as potassium salt, approximately 35.5 mmol) in ethanol (120 mL), H2SO4 (0.5 mL) is added. The mixture is stirred at 70° C. for 18 h. The pH of the clear solution is adjusted to pH 9 by adding sat. aq. NaHCO3-solution and the mixture was extracted with diethyl ether (3×300 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated to give 5-bromo-4-methyl-pyridine-2-carboxylic acid ethyl ester (8.20 g) as a green oil; LC-MS: tR=0.87 min, [M+1]+=243.91.

Workup

  1. additionis added
  2. extractionthe mixture was extracted with diethyl ether (3×300 mL)
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d5092a3198c64344946d5cb90a90d372
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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