Hydrogen Bromide → 3'-Nitro-[1,1'-biphenyl]-4-ol

HRID 1600917Notes

Reaction equation

HRID 1600917 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[N+:15]([C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 111389244'-Methoxy-3-nitro-1,1'-biphenyl

Product 1

HCID 124650873'-Nitro-[1,1'-biphenyl]-4-olYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Solid 4-methoxy-3'-nitrobiphenyl (1.63 g) was dissolved in acetic acid (25 ml) and then concentrated hydrobromic acid (48%, 25 ml) was added (CAUTION). The mixture was heated at reflux for 2 hours and was then cooled. The reaction mixture was partitioned between ether and water. The organic layer was dried over anhydrous magnesium sulfate, the solution filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:ether (9:1) to give the sub-title compound as a yellow oil (1.44 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturewas then cooled
  4. customThe reaction mixture was partitioned between ether and water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe solution filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography over silica eluting with hexane:ether (9:1)

Sources & evidence

ORD record
ord-65730d28c16e4690acb228ee744b53a2
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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