Toluene → 4-Phenyldibenzothiophene

HRID 71077Notes

Reaction equation

HRID 71077 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:18]1([C:4]2[C:5]3[S:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2734329Dibenzothiophene-4-boronic acid

Product 1

HCID 64259324-PhenyldibenzothiopheneYield 83%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

10 g (41.6 mmol) 4-dibenzothiophene boronic acid, 6.25 g (39.6 mmol) bromobenzene, 366 mg (0.39 mmol) Pd2(dba)3, 656 mg (1.6 mmol) S-phose, 25.4 g (120 mmol) K3PO4, 180 mL toluene and 20 mL water were charged in a 500 mL flask. The mixture was heated up to reflux under nitrogen for overnight. The reaction mixture was purified by silica gel column chromatography with pure hexane as elute. ˜8.5 g (83%) white solid was obtained as product which was confirmed by MS.

Workup

  1. temperatureThe mixture was heated up
  2. temperatureto reflux under nitrogen for overnight
  3. customThe reaction mixture was purified by silica gel column chromatography with pure hexane
  4. washas elute

Sources & evidence

ORD record
ord-b64dfa53f34848bc92ac610b91f165f1
Source dataset
uspto-grants-2014_09
Patent number
US08822708B2

Reaction notes

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