Hydrochloric Acid → 2,6-Dibromo-3,5-dimethoxypyridine

HRID 76096Notes

Reaction equation

HRID 76096 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Cl.[Br-:12].[K+].S(=O)(=O)(O)O.[Br:19]([O-])(=O)=O.[K+].S([O-])([O-])=O.[Na+].[Na+]>N1C=CC=CC=1.O>[Br:12][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:6]([Br:19])[N:5]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 253877Potassium Bromide2×HCID 8177333,5-DimethoxypyridineHCID 23673461Potassium Bromate2×

Product 1

HCID 33579892,6-Dibromo-3,5-dimethoxypyridineYield 83.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1049PyridineSolvent

Procedure

A flask was charged with 3,5-dimethoxypyridine (13 g; 93 mmol), water (100 mL) and concentrated hydrochloric acid (8 mL; ˜1 eq.). To a separate flask was added potassium bromide (65 g.), water (200 mL) and sulfuric acid (69 g.). To a third flask was added potassium bromate (18 g.), and water (1.2 liters). All flasks were stirred until they were homogenous. To the flask with potassium bromate was added the solution containing potassium bromide, followed by the solution containing the pyridine compound. The reaction was stirred for ten minutes, and a solution of sodium sulfite was added until the orange color disappeared. The solid was collected by Buchner funnel, washed with water, dissolved in dichloromethane, dried over sodium sulfate, and evaporated to give 2,6-dibromo-3,5-dimethoxypyridine (23.3 g; 78 mmol).

Workup

  1. stirringThe reaction was stirred for ten minutes
  2. customThe solid was collected by Buchner funnel
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-992bfb0e8f604d099931c9193a121caf
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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