Phenol → 2-Bromo-6-phenoxypyridine

HRID 2309227Notes

Reaction equation

HRID 2309227 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[N:12]=1>CN(C)C=O>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

Product 1

HCID 8245892-Bromo-6-phenoxypyridineYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6.5 g (0.135 mol) of 50% sodium hydride in 75 ml of dimethylformamide at 0° C. and under N2 was added a solution of 11.9 g (0.127 mol) of phenol in 75 ml of dimethylformamide. Once dropwise addition was complete, 30.0 g (0.127 mol) of 2,6-dibromopyridine was added in one portion and the mixture was heated at 60° to 65° C. for 18 hours. The mixture was then cooled and partitioned between ether and 1N aqueous NaOH. The ether extracts were washed two times with aqueous NaHCO3, dried over MgSO4, filtered and concentrated under vacuum. The solid residue was slurried in hexane, filtered and dried to afford 25.1 g (79%) of the title compound as a white powder: m.p. 83° to 86° C.; 1H NMR (CDCl3) δ 6.70 (d, 1H), 7.0-7.5 (m, 7 H).

Workup

  1. additionOnce dropwise addition
  2. temperaturethe mixture was heated at 60° to 65° C. for 18 hours
  3. temperatureThe mixture was then cooled
  4. custompartitioned between ether and 1N aqueous NaOH
  5. washThe ether extracts were washed two times with aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-1fb4efaaa6594a2faa84b2f54c993cdb
Source dataset
uspto-grants-1987_09
Patent number
US04694013

Reaction notes

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