1,4-Dibromobenzene → 4-(4-Bromophenyl)morpholine

HRID 1180419Notes

Reaction equation

HRID 1180419 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.CC(C)([O-])C.[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 8083MorpholineHCID 23665647Potassium tert-butoxide

Product 1

HCID 116228514-(4-Bromophenyl)morpholine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of of morpholine (0.85 mmol, 739 mg) in dioxane (12 mL) was added 1,4-dibromobenzene (21.2 mmol, 5 g), 2-(di-t-butylphosphine)biphenyl (1.02 mmol, 304 mg), potassium t-butoxide (25.5 mmol, 2.47 g) and Pd2(dba)3 (0.254 mmol, 233 mg) The mixture was degassed under a stream of nitrogen and then heated to reflux for 20 h. The mixture was diluted with EtOAc and washed with water and brine. The organic extract was concentrated under reduced pressure and the residue was chromatographed to give the desired product.

Workup

  1. customwas degassed under a stream of nitrogen
  2. temperatureheated
  3. temperatureto reflux for 20 h
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water and brine
  6. extractionThe organic extract
  7. concentrationwas concentrated under reduced pressure
  8. customthe residue was chromatographed

Sources & evidence

ORD record
ord-cd186441b715488095e373d7d5a39ec2
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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