Hydrogen Bromide → 3-Bromo-2-chloro-4-methylpyridine

HRID 1043912Notes

Reaction equation

HRID 1043912 reaction equation
N[C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[BrH:10].N([O-])=O.[Na+].BrBr>O>[Br:10][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 27563873-Amino-2-chloro-4-methylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 404251193-Bromo-2-chloro-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-amino-2-chloro-4-methylpyridine (2 g) was added to a mixed solvent of a 48% aqueous hydrogen bromide solution (17 mL) and water (12 mL). Sodium nitrite (2.5 g) was added to the solution at 0° C. Further, bromine (22 mL) was added. The reaction mixture was warmed to room temperature and stirred for 12 hours. The reaction mixture was partitioned by adding a 5 N aqueous sodium hydroxide solution and ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (1.7 g).

Workup

  1. customThe reaction mixture was partitioned
  2. additionby adding a 5 N aqueous sodium hydroxide solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd502ee03ae3404a83fc3d151ad1a670
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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