Tetrahydrofuran → 9-(5-Bromo-2-nitrophenyl)phenanthrene

HRID 513313Notes

Reaction equation

HRID 513313 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.C1COCC1.Br[C:24]1[CH:29]=[C:28]([Br:30])[CH:27]=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32].[OH-].[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.O>[Br:30][C:28]1[CH:27]=[CH:26][C:25]([N+:31]([O-:33])=[O:32])=[C:24]([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)[CH:29]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 117757049-Phenanthracenylboronic acidHCID 123156462,4-Dibromo-1-nitrobenzene

Product 1

HCID 866699709-(5-Bromo-2-nitrophenyl)phenanthreneYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A 2 L round bottom flask was charged with phenanthracene-9-boronic acid (76.61 g, 345 mmol), THF (700 mL), and H2O (350 mL), and the mixture was dissolved. To the resultant mixture, 2,4-dibromo-1-nitrobenzene (146 g, 518 mmol), NaOH (42 g, 1035 mmol), and Pd(PPh3)4 (20 g, 17.3 mmol) were sequentially added, followed by reaction at 80° C. for 24 hours. After the reaction was completed, the resultant product was extracted with methylene chloride, water, and brine, and the organic layer was dried with MgSO4. The obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as to give 80.4 g of a product (62%).

Workup

  1. dissolutionthe mixture was dissolved
  2. customfollowed by reaction at 80° C. for 24 hours
  3. extractionthe resultant product was extracted with methylene chloride, water, and brine
  4. dry with materialthe organic layer was dried with MgSO4
  5. customThe obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as

Sources & evidence

ORD record
ord-89b570ea03e74f0f93bb467c4ebd9946
Source dataset
uspto-grants-2015_08
Patent number
US09102616B2

Reaction notes

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