Hydrochloric Acid → HCID 23103379, compound

HRID 1012023Notes

Reaction equation

HRID 1012023 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[Br:6][C:7]1C=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9](C(Br)Br)[CH:8]=1.Cl>C(O)(=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][C:2]=1[CH:1]=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 23103393HCID 23103393, compound

Product 1

HCID 23103379HCID 23103379, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Bromosuccinimide (7.35 g) and benzoyl peroxide (196 mg) were added to a solution of 4-bromo-2-methylbiphenyl (5.0 g) in carbon tetrachloride (150 ml), and the mixture was stirred over night under reflux condition. After cooling to room temperature, the reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated therefrom under reduced pressure to give the residue. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 4-bromo-2-(dibromomethyl)biphenyl (7.9 g). Sodium acetate (9.6 g) was added to a solution of 4-bromo-2-(dibromomethyl)biphenyl in acetic acid (240 ml) and stirred for two days under reflux condition. After cooling to room temperature, 4M hydrochloric acid (50 ml) was added to the reaction mixture, and the resulting mixture was stirred for two hours under reflux condition. After cooling to room temperature, the solvent was evaporated therefrom under reduced pressure to give the residue, ethyl acetate was added to the resulting residue, and the resultant was washed with 1M hydrochloric acid and saturated saline solution in order and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the resulting residue was dried to obtain 4-bromo biphenyl-3-carboaldehyde (5.05 g).

Workup

  1. temperatureunder reflux condition
  2. stirringthe resulting mixture was stirred for two hours
  3. temperatureunder reflux condition
  4. temperatureAfter cooling to room temperature
  5. customthe solvent was evaporated
  6. customunder reduced pressure to give the residue, ethyl acetate
  7. additionwas added to the resulting residue
  8. washthe resultant was washed with 1M hydrochloric acid and saturated saline solution in order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was evaporated from the filtrate under reduced pressure
  12. customto give the residue
  13. customthe resulting residue was dried

Sources & evidence

ORD record
ord-28ed6ddc536e4df0a2f3d3160acc0659
Source dataset
uspto-grants-2011_07
Patent number
US07977466B2

Reaction notes

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