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

HRID 1264223Notes

Reaction equation

HRID 1264223 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O-:10].[Na+]>CS(C)=O.CCOCC>[CH3:9][O:10][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 693532,5-DibromopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 92.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,5-dibromopyridine (20 g, 84 mmol) in DMSO (84 mL) is added (25 wt %) sodium methoxide (21.2 mL, 93 mmol). The resulting solution is heated to 80° C. and stirred for 45 min then cooled to 20° C., diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ether in hexanes) to give 14.6 g of title compound as a colorless oil. 1H NMR (CDCl3) δ 3.90 (s, 3H), 6.66 (d, J=9 Hz, 1H), 7.63 (dd, J=9, 3 Hz, 1H), 8.20 (d, J=3 Hz, 1H). MS (EI) m/z 187/189 (M+, Br).

Workup

  1. temperaturethen cooled to 20° C.
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 10% ether in hexanes)

Sources & evidence

ORD record
ord-ab3ffc07949541e0a85de48888b5a8b2
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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