Phenol → 3-Bromodiphenyl ether

HRID 322025

Reaction equation

HRID 322025 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=1>CN(C=O)C.CCOCC>[Br:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 79271,3-DibromobenzeneHCID 24758Sodium hydride

Product 1

HCID 961653-Bromodiphenyl ether

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of phenol (5.08 g; 54 mmol) in 30 ml dry DMF at 0 C. was added portionwise NaH (1.98 g; 66 mmol; 80% dispersion in oil). The mixture was stirred 30 min at r.t. then 1,3-dibromobenzene (33 ml; 273 mmol) and Cu2O (3.95 g; 28 mmol) were added. The final mixture was heated to reflux for 4 h, cooled to r.t., diluted with Et2O (200 ml), washed with water (3×200 ml), NaOH (1.0 M; 2×100 ml) and brine, dried over MgSO4 and concentrated. Flash chromatography with hexane afforded the desired material.

Workup

  1. temperatureto reflux for 4 h
  2. temperaturecooled to r.t.
  3. washwashed with water (3×200 ml), NaOH (1.0 M; 2×100 ml) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf3d1ec64b6c48cfbcc2bb21844176b1
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Linked notes

Loading…