Hydrogen Bromide → HCID 10775914, compound

HRID 919186Notes

Reaction equation

HRID 919186 reaction equation
CO[C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[C:5]([O:11]C)[C:4]=1[C:13]1[C:18]([O:19]C)=[CH:17][C:16]([O:21]C)=[CH:15][C:14]=1[O:23]C.Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[OH:11][C:5]1[C:4]2[C:13]3[C:14]([OH:23])=[CH:15][C:16]([OH:21])=[CH:17][C:18]=3[O:19][C:3]=2[CH:8]=[C:7]([OH:9])[CH:6]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 52193412,2',4,4',6,6'-Hexamethoxybiphenyl

Product 1

HCID 10775914HCID 10775914, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 7 (3 g, 8.97 mmol) was refluxed for 18 h in a 20 mL solution consisting of a 1:1 mixture of HBr and acetic acid. The reaction mixture was neutralized by adding saturated aqueous NaHCO3. The subsequent mixture was then extracted with ethyl acetate and the organic layer was further washed with brine, water and dried over Na2SO4. After removing the solvent in vacuo, the brown, viscous residue was purified by column chromatography (5-20% ethyl acetate/hexane) to yield 8 (1.6 g, 77%) as a yellow solid.

Workup

  1. extractionThe subsequent mixture was then extracted with ethyl acetate
  2. washthe organic layer was further washed with brine, water
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe brown, viscous residue was purified by column chromatography (5-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cc6242d7a58146c1b06219713707eb6b
Source dataset
uspto-grants-2016_03
Patent number
US09273021B2

Reaction notes

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