Potassium Carbonate → 3-(4-Bromophenyl)-9-phenylcarbazole

HRID 516493Notes

Reaction equation

HRID 516493 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:29][C:30]1[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([C:16]2[CH:17]=[CH:18][C:19]3[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:8]4[C:13]([C:14]=3[CH:15]=2)=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole2×

Product 1

HCID 513582933-(4-Bromophenyl)-9-phenylcarbazoleYield 44%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (Compound 14) (5.0 g, 13.5 mmol), 4-bromoiodobenzene (10.76 g, 38 mmol), Pd(PPh3)4 (0.5 g, 0.43 mmol) and potassium carbonate (K2CO3)(5.52 g, 40 mmol) in dioxane/water (80 mL/15 mL) was degassed and heated at about 100° C. overnight, then worked up with ethyl acetate/brine. The organic phase was collected, dried over Na2SO4, and purified by flash column (hexanes to hexane/ethyl acetate 90:1). The main fraction was collected, concentrated, and a precipitate was filtered to give a white solid (Compound 15) (2.35 g, in 44% yield). Confirmed by LCMS (APCI): calculated for C24H17BrN (M+H): 398; Found: 398.

Workup

  1. customwas degassed
  2. customThe organic phase was collected
  3. dry with materialdried over Na2SO4
  4. custompurified by flash column (hexanes to hexane/ethyl acetate 90:1)
  5. customThe main fraction was collected
  6. concentrationconcentrated
  7. filtrationa precipitate was filtered

Sources & evidence

ORD record
ord-51241983bc27482185fe02ffef621da1
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

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