Bromine → 5-Bromo-2-methoxynicotinonitrile

HRID 334381

Reaction equation

HRID 334381 reaction equation
C([O-])(=O)C.[Na+].[Br:6]Br.[CH3:8][O:9][C:10]1[N:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13]>C(O)(=O)C>[Br:6][C:15]1[CH:16]=[N:17][C:10]([O:9][CH3:8])=[C:11]([CH:14]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24408BromineHCID 2520992-Methoxypyridine-3-carbonitrileHCID 517045Sodium Acetate

Product 1

HCID 263699225-Bromo-2-methoxynicotinonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0° C. are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70° C. overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50° C. to yield 11.6 g (73%) of 5-bromo-2-methoxy-nicotinonitrile in the form of a white solid.

Workup

  1. customAfter returning to room temperature
  2. additionthe reaction medium is added to an ice bath
  3. customthe precipitate obtained
  4. filtrationis filtered
  5. washrinsed with water
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-e5ba636fb380428d8df8fe03743b41e1
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Linked notes

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