Sodium Carbonate → HCID 23080768, compound

HRID 2274134Notes

Reaction equation

HRID 2274134 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3](B(O)O)[CH:2]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=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:20][C:21]1[CH:26]=[CH:25][C:24]([C:5]2[CH:6]=[CH:7][C:8]3[C:9]4[C:14]([C:15]5[C:16]=3[C:4]=2[CH:3]=[CH:2][CH:1]=5)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 23088535Fluoranthen-3-ylboronic acid

Product 1

HCID 23080768HCID 23080768, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In the atmosphere of argon, 9.1 g of fluoranthene-3-boronic acid, 10.5 g of 4-bromoiodobenzene, 2.1 g of tetrakis(triphenylphosphine)palladium(0), 186 mL of toluene and 74 mL of an aqueous 2M solution of sodium carbonate were placed in a flask, and stirred at 100° C. for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. After removing an aqueous phase, an organic phase was washed with saturated saline, and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and residues were purified by silica gel column chromatography, whereby 9.2 g (yield 70%) of 3-(4-bromophenyl)fluoranthene as an intended product was obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction solution was extracted with toluene
  3. customAfter removing an aqueous phase
  4. washan organic phase was washed with saturated saline
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure, and residues

Sources & evidence

ORD record
ord-6e48f012d5db44eb8ee79e18550e4d18
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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