Sodium Carbonate → HCID 59524129, compound

HRID 889785Notes

Reaction equation

HRID 889785 reaction equation
[CH:1]1[C:6]2[C:7]3[C:16]([C:17]4[C:22]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][C:14](B(O)O)=[C:13]1[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]1.[Br:26][C:27]1[CH:28]=[C:29](I)[CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:26][C:27]1[CH:28]=[C:29]([C:14]2[CH:15]=[C:16]3[C:7](=[C:8]4[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]4)[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:22]2[C:17]3=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 59582968HCID 59582968, compound

Product 1

HCID 59524129HCID 59524129, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 3.86 g of the benzo[g]chrysene-10-boronic acid which had been prepared in Synthesis Example 3, 2.83 g of 3-bromoiodobenzene, 0.231 g of tetraxis(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 then with saturated brine, and dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by a silica gel column chromatography, whereby 4.12 g (yield: 95%) of 10-(3-bromophenyl)benzo[g]chrysene was obtained.

Workup

  1. customwere placed in a flask
  2. temperatureThe resultant was refluxed
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. customan organic phase which had been separated
  6. washwas washed with water
  7. dry with materialwith saturated brine, and dried with magnesium sulfate
  8. filtrationAfter the magnesium sulfate was filtered out
  9. concentrationthe organic phase was concentrated
  10. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d5fbd452a8c744a898ede16cb3c53bcf
Source dataset
uspto-grants-2012_08
Patent number
US08253129B2

Reaction notes

Loading…