Hydrogen Bromide → 3-Bromodibenzofuran

HRID 1371843Notes

Reaction equation

HRID 1371843 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3](N)[CH:2]=1.N([O-])=O.[Na+].[BrH:19]>O.[Cu](Br)Br>[Br:19][C:3]1[CH:2]=[CH:1][C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 200613-DibenzofuranamineHCID 23668193Sodium Nitrite

Product 1

HCID 2968613-Bromodibenzofuran

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 962WaterSolvent4×

Conditions

Temperature
0 °C

Procedure

Combine N-dibenzofuran-3-ylamine (2.0 g, 10.8 mmol), water (20 ml), and conc. hydrobromic acid (6 ml). Cool to 0° C. Add a solution of sodium nitrite (0.7 g, 10.8 mmol) in water (16 ml). After 15 minutes add the mixture above to a mixture of copper bromide (1.7 g, 12.3 mmol) in water (9.2 ml) and hydrobromic acid (4 ml). Warm to ambient temperature. After 18 hours, add water and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.

Workup

  1. additionAfter 15 minutes add the mixture
  2. temperatureWarm to ambient temperature
  3. extractionextract with dichloromethane
  4. washwash sequentially with distilled water and brine
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a residue
  9. washChromatograph the residue eluting with 8:2 hexane

Sources & evidence

ORD record
ord-cb2e788ca4c849f6bf78895bba25cfea
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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