Ethanol → Ethyl 4-bromo-6-methylpicolinate

HRID 1908818Notes

Reaction equation

HRID 1908818 reaction equation
S(=O)(=O)(O)O.[K+].[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]([O-:17])=[O:16])[CH:9]=1.C([O-])(O)=O.[Na+].[CH2:23](O)[CH3:24]>>[CH2:23]([O:16][C:15]([C:10]1[CH:9]=[C:8]([Br:7])[CH:13]=[C:12]([CH3:14])[N:11]=1)=[O:17])[CH3:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate2×HCID 67027109HCID 67027109, compound

Product 1

HCID 25208981Ethyl 4-bromo-6-methylpicolinate

Conditions

Temperature
70 °C

Procedure

Sulfuric acid (5 mL) is added to a suspension of 4-bromo-6-methyl-pyridine-2-carboxylic acid potassium salt (5.03 g, 15.5 mmol) in ethanol (150 mL). The clear solution is heated to 70° C. and stirred for 18 h. The mixture is neutralised with NaHCO3 and sat. aq. NaHCO3 solution and then extracted three times with diethyl ether. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:2 to give 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester (2.42 g) as a yellow oil; LC-MS: tR=0.86 min, [M+1]+=243.96.

Workup

  1. extractionextracted three times with diethyl ether
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 3:2

Sources & evidence

ORD record
ord-543e41da6cfb48d68b71e6d772a0def9
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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