N-bromobutanimide → 5-Bromo-3-ethyl-2-methoxy-4,6-dimethylpyridine

HRID 1921336Notes

Reaction equation

HRID 1921336 reaction equation
[CH2:1]([C:3]1[C:4]([O:11][CH3:12])=[N:5][C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9])[CH3:2].[Br:13]N1C(=O)CCC1=O>CO>[Br:13][C:7]1[C:8]([CH3:9])=[C:3]([CH2:1][CH3:2])[C:4]([O:11][CH3:12])=[N:5][C:6]=1[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674923843-Ethyl-2-methoxy-4,6-dimethylpyridine

Product 1

HCID 674921695-Bromo-3-ethyl-2-methoxy-4,6-dimethylpyridineYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-ethyl-2-methoxy-4,6-dimethylpyridine (265 mg, 1.61 mmol), N-bromosuccinimide (346 mg, 1.93 mmol) and methanol (5 mL) is stirred at room temperature for 5 hr. The solvent is removed and the residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 5-bromo-3-ethyl-2-methoxy-4,6-dimethylpyridine (285 mg, 73%) as a white semi-solid. LC/MS: MS m/e=244/246 (M+H); RT 4.78 min.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by chromatography
  3. washeluting with dichloromethane
  4. additionProduct containing fractions
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-019ba591972d44d7856d0a294983740c
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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