1-Bromo-4-iodobenzene → HCID 86696082, compound

HRID 2172408Notes

Reaction equation

HRID 2172408 reaction equation
[C:1]1([NH:7][C:8]2[C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][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.CC([O-])(C)C.[Na+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 23676156Sodium t-butoxideHCID 67436692HCID 67436692, compound

Product 1

HCID 86696082HCID 86696082, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Toluene (125 mL) was bubbled with nitrogen gas for 15 minutes, and subsequently 1,1′-Bis(diphenylphosphino)ferrocene (0.2 g, 0.4 mmol) and Pd2(dba)3 (0.1 g, 0.1 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes, then N-phenyldibenzo[b,d]thiophen-4-amine (3.2 g, 11.6 mmol), 1-bromo-4-iodobenzene (4.5 g, 15.9 mmol), NaOtBu (1.5 g, 15.6 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes and refluxed for 12 hours. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% CH2Cl2/hexane. The solvent was removed in vacuo and the residue was purified by flash chromatography using 10-15% CH2Cl2/hexane to afford N-(4-bromophenyl)-N-phenyldibenzo[b,d]thiophen-4-amine (4.0 g, 80% yield) as a white solid.

Workup

  1. customToluene (125 mL) was bubbled with nitrogen gas for 15 minutes
  2. customThe mixture was bubbled with nitrogen gas for 15 minutes
  3. customThe mixture was bubbled with nitrogen gas for 15 minutes
  4. temperaturerefluxed for 12 hours
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with 50% CH2Cl2/hexane
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a96901ba2ca0417baa226bc39ea93d64
Source dataset
uspto-grants-2015_06
Patent number
US09054323B2

Reaction notes

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