Carbazole → 9-(3-Bromophenyl)-9H-carbazole

HRID 2039416Notes

Reaction equation

HRID 2039416 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:16]=[C:17]([Br:21])[CH:18]=[CH:19][CH:20]=1.[Na]>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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1(C)C(C)=CC=CC=1>[Br:21][C:17]1[CH:16]=[C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 11561Benzene, 1-bromo-3-iodo-HCID 5360545Sodium

Product 1

HCID 586908889-(3-Bromophenyl)-9H-carbazoleYield 41.3%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

The 200 ml round-bottom flask equipped with reflux condenser and magnetic stirrer was charged with carbazole (14.75 g, 88 mmol), 3-iodobromobenzene (25.0 g, 88 mmol), Pd2(dba)3 (0.8 g, 0.85 mmol) and dppf (1,1′-bis(diphenylphosphino)ferrocene, 0.98 g, 1.8 mmol), sodium t-buthoxide (25 g, 265 mmol) and 100 ml of dry xylene. Reaction mixture was refluxed under N2 atmosphere for 48 hours, cooled down to room temperature and evaporated. The solid residue was subjected to column chromatography on silica (eluent—hexane/ethyl acetate 9/1) providing 11.7 g of 9-(3-bromophenyl)-9H-carbazole as white solid.

Workup

  1. customThe 200 ml round-bottom flask equipped
  2. temperaturewith reflux condenser and magnetic stirrer
  3. customReaction mixture
  4. temperaturewas refluxed under N2 atmosphere for 48 hours
  5. customevaporated

Sources & evidence

ORD record
ord-90d40c73b32a4dcf8d9935debd946bb5
Source dataset
uspto-grants-2013_11
Patent number
US08580402B2

Reaction notes

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