3-Bromo-2-chloro-6-methylpyridine → 3-Bromo-2-methoxy-6-methylpyridine

HRID 1518962Notes

Reaction equation

HRID 1518962 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:10][O-:11].[Na+]>O1CCCC1>[Br:1][C:2]1[C:3]([O:11][CH3:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27344183-Bromo-2-chloro-6-methylpyridineHCID 10942334Sodium Methoxide2×

Product 1

HCID 219525873-Bromo-2-methoxy-6-methylpyridineYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 3-bromo-2-chloro-6-methylpyridine (300 mg, 1.45 mmol) in tetrahydrofuran (20 mL), add sodium methoxide (1.57 g, 29 mmol), slowly with stirring. Allow the mixture to warm to ambient temperature and stir overnight. Add additional sodium methoxide (500 mg) and stir at 100° C. overnight. Quench with water (20 mL), extract three times with ethyl acetate (30 mL). Combine the organics and wash with water then brine, and dry over sodium sulphate. Filter and concentrate to give the title product as a yellow solid (135 mg, 46%). 1HNMR (MeOH-d4): δ 7.72 (d, 1H), 6.70 (d, 1H), 3.93 (s, 3H), 2.38 (s, 3H).

Workup

  1. stirringstir overnight
  2. stirringstir at 100° C. overnight
  3. customQuench with water (20 mL)
  4. extractionextract three times with ethyl acetate (30 mL)
  5. washCombine the organics and wash with water
  6. dry with materialbrine, and dry over sodium sulphate
  7. filtrationFilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-8d366de7535d4acfbe9c4cc74166b2f9
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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