Methanesulfonic Acid → 5-Bromobenzo[c]phenanthrene

HRID 1890208Notes

Reaction equation

HRID 1890208 reaction equation
[Br:1][C:2]1C2C(=CC=CC=2)[C:5]([C:12]2(C=COC)[CH:17]=[CH:16][CH:15]=[CH:14][CH2:13]2)=[CH:4][CH:3]=1.CS(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:1][C:2]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:5]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH:5]=[CH:4][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 684333991-Bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene

Product 1

HCID 106624825-Bromobenzo[c]phenanthreneYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

180 g of the 1-bromo-4-[1-(2-methoxyvinyl) phenyl]naphthalene obtained and 1.0 L of dichloromethane were placed in a flask. During stirring at room temperature, 25 mL of methanesulfonic acid were added to the flask. Stirring was conducted at room temperature for 8 hours. After the completion of the reaction, 1 L of a 10% aqueous solution of potassium carbonate was added. An aqueous phase was removed and an organic phase which had been separated was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 24.4 g (yield: 15%) of 5-bromobenzo[c]phenanthrene was obtained.

Workup

  1. stirringStirring
  2. additionwas added
  3. customAn aqueous phase was removed
  4. customan organic phase which had been separated
  5. washwas washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationAfter the magnesium sulfate was filtered out
  8. concentrationthe organic phase was concentrated
  9. customThe resulting residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-c11ece98b8794a4a86ef97a8688a2e82
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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