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

HRID 68496Notes

Reaction equation

HRID 68496 reaction equation
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1B(O)O.[Br:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:7]5[CH:3]=[CH:2][CH:1]=[CH:14][C:8]=5[CH:9]=[CH:10][C:11]=4[CH:12]=[CH:13][C:14]=3[CH:1]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 46835781Phenanthren-2-ylboronic acid

Product 1

HCID 8664913610-(3-Bromophenyl)benzo[c]phenanthreneYield 158.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 22.2 g of phenanthrene-2-boronic acid, 28.3 g of 4-bromoiodobenzene, 2.31 g of tetrakis(triphenyl phosphine) palladium(0), 400 mL of toluene, and 200 mL of a 2-M aqueous solution of sodium carbonate were loaded, and then the mixture was stirred for 8 hours under reflux. After having been cooled to room temperature, the reaction solution was extracted with toluene. The water layer was removed, and the organic layer was sequentially washed with water and a saturated salt solution, and was then dried with magnesium sulfate. After magnesium sulfate had been separated by filtration, the organic layer was concentrated. The residue was purified by silica gel column chromatography. Thus, 30.3 g of 10-(3-bromophenyl)benzo[c]phenanthrene were obtained (91%).

Workup

  1. temperatureunder reflux
  2. extractionthe reaction solution was extracted with toluene
  3. customThe water layer was removed
  4. washthe organic layer was sequentially washed with water
  5. dry with materiala saturated salt solution, and was then dried with magnesium sulfate
  6. customAfter magnesium sulfate had been separated by filtration
  7. concentrationthe organic layer was concentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-071fb915539e455fb8e11aa1d9dc2550
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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