Toluene → 5-(3-Bromophenyl)benzo[c]phenanthrene

HRID 1429332Notes

Reaction equation

HRID 1429332 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.C1(C)C=CC=CC=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.O.C(COC)OC>[Br:22][C:23]1[CH:24]=[C:25]([C:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]3[C:18]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[CH:6]=[CH:7][C:8]=3[CH:9]=2)[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 59622711Benzo[c]phenanthren-5-ylboronic acid

Product 1

HCID 595240805-(3-Bromophenyl)benzo[c]phenanthreneYield 63.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In argon atmosphere, a mixture of 6.32 g (22.3 mmol) of 5-benzo[c]phenanthreneboronic acid, 5.07 g (18.6 mmol) of 3-bromoiodobenzene, 1.29 g (1.12 mmol) of tetrakis(triphenylphosphine)palladium (0), 80 ml of toluene, 80 ml of dimethoxyethane, and 33.8 g of a 2 M sodium carbonate aqueous solution was refluxed for 8 h under stirring. After the reaction, the reaction mixture was added with water and extracted with toluene. The organic phase was washed with water and dried over sodium sulfate, and then the toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 4.53 g (yield: 56.8%) of 5-(3-bromophenyl)benzo[c]phenanthrene.

Workup

  1. temperaturewas refluxed for 8 h
  2. customAfter the reaction
  3. extractionextracted with toluene
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe toluene was removed by distillation under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c56114a24f4b479d87775dac3ae7c6ae
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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