Hydrogen Bromide → HCID 343262, compound

HRID 1723276Notes

Reaction equation

HRID 1723276 reaction equation
C(O[CH2:5][C:6]1[CH:19]=[CH:18][C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[CH:12][C:11]([CH3:20])=[N:10]3)[N:7]=1)(=O)C.[BrH:21]>>[Br:21][CH2:5][C:6]1[CH:19]=[CH:18][C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[CH:12][C:11]([CH3:20])=[N:10]3)[N:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 14318419HCID 14318419, compound

Product 1

HCID 343262HCID 343262, compoundYield 42%

Procedure

The acetate (21) was dissolved in 60 mL of 31% HBr in HoAc and refluxed for 4 hours. After cooling, all the solvent was removed in vacuo. The resulting black residue was suspended in a mixture of CH2Cl2 and dilute aqueous NaHCO3. Four 200 mL CH2Cl2 extracts removed the desired bromide from the insoluble material floating at the solvent interface. After drying over Na2SO4 and removal of the solvent, the dark residual solid was relatively pure phenanthroline (22) containing a trace amount of 2,9-dimethyl-1,10-phenanthroline. The dark impurities were removed by chromatography on silica gel using CH2Cl2 as the eluent which gave 3.5 g (42%) of 22. 1H NMR (CDCl3) 2.9 (s, 3H); 4.94 (s, 2H), 7.43 (ABq, 1H, J=9 Hz), 7.6 (s, 2H); 7.8 (ABq, 1H, J=9 Hz); 7.97 (ABq, J=9 Hz); 8.1 (ABq, 1H, J=9 Hz).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling
  3. customall the solvent was removed in vacuo
  4. additionThe resulting black residue was suspended in a mixture of CH2Cl2 and dilute aqueous NaHCO3
  5. customFour 200 mL CH2Cl2 extracts removed the desired bromide from the insoluble material
  6. dry with materialAfter drying over Na2SO4 and removal of the solvent
  7. additioncontaining a trace amount of 2,9-dimethyl-1,10-phenanthroline
  8. customThe dark impurities were removed by chromatography on silica gel

Sources & evidence

ORD record
ord-985182e81a744fda8e3982335a08fe1e
Source dataset
uspto-grants-1989_08
Patent number
US04859777

Reaction notes

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