Pyridine → tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

HRID 333874Notes

Reaction equation

HRID 333874 reaction equation
[Cl:1][C:2]1(C(O)=O)[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][NH:3]1.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=CC(S(Cl)(=O)=O)=C[CH:19]=1.[C:29]([O-:32])(O)=[O:30].[Na+]>C(O)(C)(C)C>[Br:8][C:5]1[C:4]([C:29]([O:32][C:18]([CH3:28])([CH3:23])[CH3:19])=[O:30])=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86644327HCID 86644327, compound

Product 1

HCID 59447676tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-chloro-5-bromo picolinic acid (4 g) and pyridine (9.2 mL) in t-butanol (33 mL) at 0° C. was added p-toluenesulfonyl chloride (7.7 g). The resulting mixture was stirred at room temperature for 12 hours. Saturated aqueous NaHCO3 solution was added, and the resulting mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to provide the title compound.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-425017304d084deeb129fc7d06deb30f
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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