Methanesulfonic Acid → 5-Bromobenzo[c]phenanthrene

HRID 2405459Notes

Reaction equation

HRID 2405459 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[CH:19]OC)=[CH:4][CH:3]=1.CS(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:18]=[CH:19][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 676074951-Bromo-4-[2-(2-methoxyvinyl)phenyl]naphthalene

Product 1

HCID 106624825-Bromobenzo[c]phenanthreneYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction vessel was charged with 180 g of 1-bromo-4-[2-(2-methoxyvinyl)phenyl]naphthalene and 1.0 L of dichloromethane. 25 mL of methanesulfonic acid was added to the mixture at room temperature with stirring. The mixture was stirred at room temperature for 8 hours. After completion of the reaction, 1 L of a 10% potassium carbonate aqueous solution was added to the mixture. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The residue was purified by silica gel column chromatography to obtain 24.4 g of the target 5-bromobenzo[c]phenanthrene (yield: 15%).

Workup

  1. stirringThe mixture was stirred at room temperature for 8 hours
  2. additionwas added to the mixture
  3. customAfter removing the aqueous phase
  4. washthe organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  6. customAfter removing magnesium sulfate
  7. filtrationby filtration
  8. concentrationthe organic phase was concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff606c0e99c74b8a8c46bb0b36d49424
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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