Phenol → 3-Bromodiphenyl ether

HRID 2109373Notes

Reaction equation

HRID 2109373 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>[Cu].C1(C)C=CC=CC=1>[O:15]([C:2]1[CH:3]=[C:4]([Br:8])[CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 79271,3-DibromobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 961653-Bromodiphenyl etherYield 36.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 1,3-dibromobenzene (15.7 g), phenol (8.0 g), potassium hydroxide (3.8 g, mortar-ground) and copper powder (0.1 g) was heated at reflux for 18 hours at 210° C. After cooling, the reaction mixture was mixed with toluene and successively washed with 10% aqueous sodium hydroxide and water. The toluene was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane), thereby giving 6.1 g of the desired compound.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. washsuccessively washed with 10% aqueous sodium hydroxide and water
  4. customThe toluene was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane)

Sources & evidence

ORD record
ord-0ca7b70abcff4000991a7902ada59f02
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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