Carbazole → 9-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

HRID 921601

Reaction equation

HRID 921601 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[Na+].I[C:8]1[CH:9]=[C:10]([Br:14])[CH:11]=[CH:12][CH:13]=1.[CH:15]1[C:27]2[NH:26][C:25]3[C:20](=[CH:21]C=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=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.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]>[C:2]1([C:5]2[CH:23]=[CH:24][C:25]3[N:26]([C:8]4[CH:9]=[C:10]([Br:14])[CH:11]=[CH:12][CH:13]=4)[C:27]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][C:17]([C:15]2[CH:27]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:16][CH:15]=4)[CH:3]=[CH:25][CH:20]=[CH:21][CH:1]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 11561Benzene, 1-bromo-3-iodo-HCID 23676156Sodium t-butoxide

Product 1

HCID 581422319-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

Reagents, catalysts & solvents 2

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

Procedure

Mix together 0.4 g Pd2DBA3 and 0.4 g DPPF and 4.3 g sodium t-butoxide and dissolve into 200 mL xylenes in glove box. Stir 15 mins then add 25 g of 3-iodo-bromobenzene. Stir 15 mins then add 10 g carbazole and the mix brought to reflux. Reflux o/n. using an air condensor. Solution immediately is dark purple/brown but on reaching ˜80 C. it is dark reddish brown and cloudy. After heating close to reflux overnight, the solution is dark brown and clear. Evaporated outside the glove box in rotovap and then dissolved in DCM and extracted (soxhlet) through a bed of silica and basic alumina (stacked in soxhlet) using DCM. Collect dark orange solution and evaporate to dryness. Leaves a dark orange oil. Wash with methanol and then dissolve into ether and reprecipitate with methanol.

Workup

  1. stirringStir 15 mins
  2. temperatureto reflux
  3. temperatureReflux o/n
  4. temperatureAfter heating
  5. customclose
  6. temperatureto reflux overnight
  7. customEvaporated outside the glove box in rotovap
  8. dissolutiondissolved in DCM
  9. extractionextracted (soxhlet) through a bed of silica and basic alumina (stacked in soxhlet)
  10. customCollect dark orange solution
  11. customevaporate to dryness
  12. customLeaves a dark orange oil
  13. washWash with methanol
  14. dissolutiondissolve into ether and reprecipitate with methanol

Sources & evidence

ORD record
ord-c1a5272316a74904a40229974293cdfc
Source dataset
uspto-grants-2016_03
Patent number
US09276217B2

Linked notes

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