Bromine → 5-Bromo-2,3-dimethoxypyridine

HRID 2275404Notes

Reaction equation

HRID 2275404 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])(O)=O.[Na+].[Br:16]Br>C(Cl)Cl>[Br:16][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 46578092,3-Dimethoxypyridine

Product 1

HCID 125630845-Bromo-2,3-dimethoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-dimethoxy-pyridine (104 g) in DCM (1 L) and a saturated aqueous solution of NaHCO3 (1.6 ml) at 0° C. was added bromine (120 g). The reaction was stirred for 2 hours at 0° C. The reaction mixture was quenched with Na2SO3 (saturated in water, 500 ml) and stirred for 30 min. The aqueous layer was extracted with DCM, and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography on silica gel with heptane and increasing amounts of ethyl acetate.

Workup

  1. customThe reaction mixture was quenched with Na2SO3 (saturated in water, 500 ml)
  2. stirringstirred for 30 min
  3. extractionThe aqueous layer was extracted with DCM
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel with heptane
  9. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-0800420bb3d34758a11f4dc7b378c05e
Source dataset
uspto-grants-2015_09
Patent number
US09127007B2

Reaction notes

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