Sodium Carbonate → 9-(4-Bromo-2-nitrophenyl)phenanthrene

HRID 513314Notes

Reaction equation

HRID 513314 reaction equation
B(O)(O)[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27].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:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[C:15]3[C:10]([C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[CH:3]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:20]([N+:26]([O-:28])=[O:27])[CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 770041,4-Dibromo-2-nitrobenzeneHCID 117757049-Phenanthracenylboronic acid

Product 1

HCID 866699719-(4-Bromo-2-nitrophenyl)phenanthrene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A 500 mL round bottom flask was charged with toluene (250 mL), phenanthracene-9-boronic acid (18.2 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).

Sources & evidence

ORD record
ord-ca3140e8006f486a8305514f6a242292
Source dataset
uspto-grants-2015_08
Patent number
US09102616B2

Reaction notes

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