2,5-Dibromopyridine → 5-Bromo-2-methoxypyridine

HRID 2356924Notes

Reaction equation

HRID 2356924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][OH:10].C[O-].[Na+]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:10][CH3:9])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 693532,5-DibromopyridineHCID 23694274Sodium methanolate methanol

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 100.8%

Procedure

2,5-Dibromopyridine (200 g) and 28% sodium methoxide methanol solution (1535 g) were heated under reflux for 30 minutes, followed by cooling to room temperature. The mixture was partitioned between water (1.6 L) and tert-butylmethyl ether (1.6 L). The resulting organic layer was washed with brine (1 L) for 3 times, and then dried over anhydrous magnesium sulfate overnight. The dried organic layer was evaporated at 65° C., to give 160 g (96%) of the title compound as a brown oil.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe mixture was partitioned between water (1.6 L) and tert-butylmethyl ether (1.6 L)
  3. washThe resulting organic layer was washed with brine (1 L) for 3 times
  4. dry with materialdried over anhydrous magnesium sulfate overnight
  5. customThe dried organic layer was evaporated at 65° C.

Sources & evidence

ORD record
ord-f8516d713ca54261b851e909eba98e0e
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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