Phenol → 3-Bromodiphenyl ether

HRID 29068

Reaction equation

HRID 29068 reaction equation
C(N[C@H](C1C=CC=CC=1)C)CC=C.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Br:21].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.[Cu-]=O>[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:15]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 114141,2-DibromobenzeneHCID 10559173But-3-enyl-((S)-1-phenyl-ethyl)-amine

Product 1

HCID 961653-Bromodiphenyl etherYield 53%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

1-Bromo-3-phenoxy-benzene (A) A mixture of dibromobenzene (3 g, 12.75 mmol), phenol (1 g, 10.6 mmol), copper(I) oxide (152 mgs, 1 mmol), and cesium carbonate (3.46 g, 10.6 mmol) in 8 mL of NMP is heated at 195° C. for 20 minutes in a microwave. The heterogeneous mixture is filtered through a bed of Celite and the residue is washed with EtOAc (1×20 mL). The filtrate is diluted with 1N NaOH (200 mL) and extracted with EtOAc (3×100 mL). The organics were combined, dried over Na2SO4, filtered and concentrated under reduced pressures to give crude product as a yellow oil which is purified by column chromatography (100% hexanes) to give 1-bromo-3-phenoxy-benzene as a colorless oil (1.4 g, 53%). LCMS m/z 250 (M+1).

Workup

  1. filtrationThe heterogeneous mixture is filtered through a bed of Celite
  2. washthe residue is washed with EtOAc (1×20 mL)
  3. additionThe filtrate is diluted with 1N NaOH (200 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressures
  8. customto give crude product as a yellow oil which
  9. customis purified by column chromatography (100% hexanes)

Sources & evidence

ORD record
ord-1ec6e12902da4d58a1a61dc46f845bd1
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Linked notes

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