Toluene → 4-Bromo-2-methoxypyridine

HRID 337669Notes

Reaction equation

HRID 337669 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[CH3:9][O-:10].[Na+].C1(C)C=CC=CC=1>O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:10][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 38477704-Bromo-2-chloropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 140623094-Bromo-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-2-chloropyridine, sodium methoxide (1.6 equiv.) and toluene (6.1 volumes) were heated to 95° C. for 40 h. Toluene (6.1 volumes) and water (3 volumes) were added and the lower aqueous phase cut away. The organic was washed with water (1.5 volumes) and then the volatiles evaporated to give the title compound as an oil. HRMS (ES, M+H) Calcd 187.9711. Found 187.9711.

Workup

  1. washThe organic was washed with water (1.5 volumes)
  2. customthe volatiles evaporated

Sources & evidence

ORD record
ord-d4355942cb0447278fa4b6fa160cb7ba
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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