Toluene → HCID 15688873, compound

HRID 513317Notes

Reaction equation

[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(B(O)O)C=CC=CC=1.Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>O.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>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A 500 mL round bottom flask was charged with toluene (250 mL), phenyl boronic acid (10 g, 82 mmol), 2,5-dibromonitrobenzene (23.1 g, 82.3 mmol), Pd(PPh3)4 (2.8 g, 2.5 mmol), and 2M Na2CO3 aqueous solution (124 mL). Then, at 90° C., the mixture was heated under reflux for 6 hours. After the reaction was completed, the resultant product was diluted with addition of distilled water at room temperature. Then, the resultant product was extracted with methylene chloride and water. The organic layer was dried with MgSO4, and concentrated. Then, the produced compound was purified by silica gel column (methylene chloride:hexane=1:1) to give 19.2 g of a product (84.2%).

Workup

temperatureunder reflux for 6 hours
extractionThen, the resultant product was extracted with methylene chloride and water
dry with materialThe organic layer was dried with MgSO4
concentrationconcentrated
customThen, the produced compound was purified by silica gel column (methylene chloride:hexane=1:1)

Sources & evidence

ORD record: ord-948cea6ecac74a6ebdf48987a9adf002
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102616B2

Reaction notes

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