1,3-Dibromobenzene → 9-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole

HRID 1848964Notes

Reaction equation

HRID 1848964 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[C:19]([N:23]3[C:35]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:29]4[C:24]3=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:20]=[CH:21][CH:22]=2)O1.C([O-])(=O)C.[K+]>C1(C)C=CC=CC=1.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:8][C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[CH:17][CH:18]=[C:19]([N:23]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[C:30]4[C:35]3=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:20]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 517044Potassium AcetateHCID 58690899(3-(carbazole-9H)Phenyl)Pinacol ester

Product 1

HCID 588711539-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Step3. 1,3-Dibromobenzene (16 g, 64.9 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole b(6.0 g, 11.6 mmol), potassium acetate (saturated solution of 6.6 g in water) and tetrakis(triphenylphosphine)palladium (0) (380 mg) are heated to reflux in 150 mL of toluene overnight under nitrogen atmosphere. After cooling down, evaporation and column chromatography 9-(3′-bromo-[1,1′-biphenyl]-3-yl)-9H-carbazole (5.8 g) is obtained.

Workup

  1. temperatureAfter cooling down
  2. customevaporation

Sources & evidence

ORD record
ord-8a6e108f080245799b4a461477517e82
Source dataset
uspto-grants-2015_02
Patent number
US08952363B2

Reaction notes

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