Sodium Carbonate → HCID 59524089, compound

HRID 2405461Notes

Reaction equation

HRID 2405461 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.I[C:21]1[CH:22]=[C:23]([Br:27])[CH:24]=[CH:25][CH:26]=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:27][C:23]1[CH:22]=[C:21]([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:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 23088535Fluoranthen-3-ylboronic acid

Product 1

HCID 59524089HCID 59524089, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 9.1 g of fluoranthene-3-boronic acid, 10.5 g of 3-iodobromobenzene, 2.1 g of tetrakis(triphenylphosphine)palladium(0), 186 mL of toluene, and 74 mL of a 2 M sodium carbonate aqueous solution in an argon atmosphere. The mixture was stirred at 100° C. for 8 hours. After cooling the reaction solution to room temperature, the reaction solution was extracted with toluene. After removing the aqueous phase, the organic phase was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtering the organic phase, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 9.2 g of the target 3-(3-bromophenyl)fluoranthene (yield: 70%).

Workup

  1. temperatureAfter cooling the reaction solution to room temperature
  2. extractionthe reaction solution was extracted with toluene
  3. customAfter removing the aqueous phase
  4. washthe organic phase was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtering the organic phase
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2dde44e9ba5c404892286e368d2fc0db
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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