Toluene → HCID 68001716, compound

HRID 571593Notes

Reaction equation

HRID 571593 reaction equation
Br[C:2]1[C:12](Br)=[CH:11][C:10]2[C:14]3[C:3]=1[C:4](=[O:16])[C:5](=[O:15])[C:6]=3[CH:7]=[CH:8][CH:9]=2.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:32]1(C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)C>[C:17]1([C:2]2[C:12]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:11][C:10]3[C:14]4[C:3]=2[C:4](=[O:16])[C:5](=[O:15])[C:6]=4[CH:7]=[CH:8][CH:9]=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68001708HCID 68001708, compound

Product 1

HCID 68001716HCID 68001716, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 6.8 g (20 mmol) of 3,4-dibromoacenaphthenequinone, 6.1 g (50 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 3.85 g (11.5 mmol) of 3,4-diphenylacenaphthenequinone. The yield was 57.5%.

Workup

  1. customto react at 90° C. for 12 hours
  2. customthe organic layer was separated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-4dee7911b1284499adbc7367e84c3543
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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