Hydrogen Bromide → [1,1-Biphenyl]-3-carbaldehyde,4,5-dihydroxy-

HRID 218254Notes

Reaction equation

HRID 218254 reaction equation
C[O:2][C:3]1[C:10]([O:11]C)=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:4]=1[CH:5]=[O:6].Br>C(O)(=O)C>[OH:2][C:3]1[C:10]([OH:11])=[CH:9][C:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 820388002,3-Dimethoxy-5-phenylbenzaldehyde

Product 1

HCID 45093328[1,1-Biphenyl]-3-carbaldehyde,4,5-dihydroxy-Yield 52.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 21 (0.63 g; 2.6 mmol), 48% aqueous hydrobromic acid (15 mL) and acetic acid (12 mL) was stirred under nitrogen at reflux overnight. The suspension was decanted from dark solid and evaporated. The residue was taken up in boiling dichloromethane (three lots of 50 mL), filtered hot and evaporated giving 22 as pale brown solid (0.290 g):

Workup

  1. temperatureat reflux overnight
  2. customThe suspension was decanted from dark solid
  3. customevaporated
  4. filtrationfiltered hot
  5. customevaporated

Sources & evidence

ORD record
ord-7d92c83a098f4cb4a0e31b0d93e853e3
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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