Sodium Carbonate → 5-(4-Bromophenyl)acenaphthene

HRID 1785600Notes

Reaction equation

HRID 1785600 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6](B(O)O)=[CH:5][CH:4]=[C:3]3[CH2:2]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=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:16][C:17]1[CH:22]=[CH:21][C:20]([C:6]2[C:7]3[C:12]4[C:3]([CH2:2][CH2:1][C:11]=4[CH:10]=[CH:9][CH:8]=3)=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 3573835Acenaphthene-5-boronic acid

Product 1

HCID 575959355-(4-Bromophenyl)acenaphtheneYield 100%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Five point nine gram of the 5-acenaphthene boronic acid obtained and 10.2 gram of 4-bromo iodobenzene were dissolved into 100 milliliter of toluene. Further adding tetrakistriphenylphosphinepalladium in an amount of 1.7 g and 2M-sodium carbonate aqueous solution in an amount of 45 milliliter, an atmospheric air was replaced with argon gas. The resultant solution was refluxed under heating for 6 hours, cooled by leaving it standing and the organic layer was extracted with the use of toluene. Washing with the use of a saturated sodium chloride solution, the organic layer was dried with anhydrous sodium sulfate, and the organic solvent was distillated by means of an evaporator. After refining the residues by means of silicagel column chromatography (spreading solvent: hexane), 9.2 g of the aimed intermediate product 5-(4-bromophenyl) acenaphthene as a pale yellow solid was obtained (yield: 100%).

Workup

  1. temperatureunder heating for 6 hours
  2. temperaturecooled
  3. customby leaving it
  4. extractionthe organic layer was extracted with the use of toluene
  5. washWashing with the use of a saturated sodium chloride solution
  6. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  7. customthe organic solvent was distillated by means of an evaporator

Sources & evidence

ORD record
ord-a1164ab4d036488f946a39cdbfdcd8e0
Source dataset
uspto-grants-2009_03
Patent number
US07504526B2

Reaction notes

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