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1-Bromo-4-iodobenzene → N-(4-bromophenyl)-N-phenyldibenzo[b,d]furan-2-amine

HRID 634545
Notes
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Reaction equation

HRID 634545 reaction equation
[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 115221-Bromo-4-iodobenzeneHCID 11776TriphenylphosphineHCID 23676156Sodium t-butoxideHCID 67204676N-phenyl-2-Dibenzofuranamine

Product 1

HCID 89769866N-(4-bromophenyl)-N-phenyldibenzo[b,d]furan-2-amine

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent

Procedure

N-phenyldibenzo[b,d]furan-2-amine (5.0 g, 19.3 mmol), and 1-bromo-4-iodobenzene (10.9 g, 38.6 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd(OAc)2 (0.22 g, 1.0 mmol), triphenylphosphine (0.51 g, 1.9 mmol) and sodium t-butoxide (2.2 g, 23.1 mmol) were added. The mixture was refluxed overnight under nitrogen.

Workup

  1. customThe solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen

Sources & evidence

ORD record
ord-1c5cdda3037f445b8d564d9d3d53e2d2
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09324949B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes