Potassium Hydroxide → 5-Bromo-2,4-dimethoxypyridine

HRID 1948240Notes

Reaction equation

HRID 1948240 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1.[Br:13]Br>O.[K+].[Br-]>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([O:4][CH3:3])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24408BromineHCID 8177312,4-dimethoxypyridine

Product 1

HCID 187887085-Bromo-2,4-dimethoxypyridineYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 253877Potassium BromideSolvent

Procedure

According to Scheme 23 Step 2: To a solution of KOH (0.5 eq, 0.8 mmol, 40 mg) in water (75 mL) was added 2,4-dimethoxypyridine (1 eq, 2.00 mmol, 0.21 g) followed by the dropwise addition of Br2 (1 eq, 2.00 mmol, 0.20 g) in 1M aqueous KBr solution (75 mL). The reaction was stirred at room temperature for 5 hours and then poured onto water (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated under reduced pressure to afford 5-bromo-2,4-dimethoxypyridine (1.40 mmol, 0.30 g, 70%) as a colorless oil. The crude product was reacted on.

Workup

  1. additionpoured onto water (10 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b916d5ddb70b4b1f919489a5069259ac
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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