Sodium Carbonate → 10-(3-Bromophenyl)benzo[c]phenanthrene

HRID 1890210Notes

Reaction equation

HRID 1890210 reaction equation
[CH:1]1[C:18]2[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:10]=[CH:9][C:8]=3[CH:7]=[C:6](B(O)O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:22][C:23]1[CH:24]=[C:25](I)[CH:26]=[CH:27][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:22][C:23]1[CH:24]=[C:25]([C:3]2[CH:2]=[CH:1][C:18]3[C:17]4[C:16]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=5[CH:10]=[CH:9][C:8]=4[CH:7]=[CH:6][C:5]=3[CH:4]=2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 59622711Benzo[c]phenanthren-5-ylboronic acid

Product 1

HCID 8664913610-(3-Bromophenyl)benzo[c]phenanthreneYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 3.26 g of the benzo[c]phenanthrene-5-boronic acid obtained, 2.83 g of 3-bromoiodobenzene, 0.231 g of tetrakis(triphenylphosphine)palladium(0), 40 mL of toluene and 20 mL of a 2M aqueous solution of sodium carbonate were placed in a flask. The resultant was refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed and an organic phase which had been separated was washed with water and saturated brine sequentially, 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 3.64 g (yield: 95%) of 10-(3-bromophenyl)benzo[c]phenanthrene was obtained.

Workup

  1. temperatureThe resultant was refluxed
  2. extractionthe reaction solution was extracted with toluene
  3. customAn aqueous phase was removed
  4. customan organic phase which had been separated
  5. washwas washed with water and saturated brine sequentially
  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-43c87789c29e4cbdae4709ff46da8030
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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