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Tetrafluoroboric acid → 3-Bromo-6-fluoro-2,4-dimethylpyridine

HRID 1043915
Notes
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Reaction equation

HRID 1043915 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.N([O-])=O.[Na+].[F:15][B-](F)(F)F.[H+]>O>[Br:9][C:5]1[C:4]([CH3:10])=[N:3][C:2]([F:15])=[CH:7][C:6]=1[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 110308555-Bromo-4,6-dimethylpyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 689735143-Bromo-6-fluoro-2,4-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-amino-5-bromo-4,6-dimethylpyridine (2 g) was suspended in fluoroboric acid (48% aqueous solution, 7.5 mL). Sodium nitrite (890 mg) dissolved in water (3 mL) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes. The precipitated solid was collected by filtration and suspended in n-heptane (100 mL). The solution was stirred with heating under reflux for two hours. After cooling to room temperature, the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to give the title compound (500 mg).

Workup

  1. additionwas added to the solution at 0° C
  2. filtrationThe precipitated solid was collected by filtration
  3. stirringThe solution was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for two hours
  6. temperatureAfter cooling to room temperature
  7. filtrationthe precipitated solid was collected by filtration
  8. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-e59142eaa1af4fccb70993bcebb01828
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563565B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes