Benzene → Biphenyl

HRID 2054725Notes

Reaction equation

HRID 2054725 reaction equation
C1C=CC=CC=1.CCN(CCO[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=C[CH:20]=1)CC.Cl.CCCCCCCCCCCC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(I)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.COCCOC>[C:22]1([C:21]2[CH:20]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 241BenzeneHCID 8182DodecaneHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 175534Tesmilifene Hydrochloride

Product 1

HCID 7095BiphenylYield 85.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Closed system: To a J. Young NMR tube, in a glove box, was added benzene (437 mg, 5.60 mmol), Ir(COD)(indenyl) (3.0 mg, 0.0070 mmol), dppe (2.8 mg, 0.0070 mmol), dodecane (internal standard, 11.5 mg, 0.0675 mmol), and HBPin (45 mg, 0.352 mmol). The tube was sealed, removed from the box, and stirred at 100° C. for 18 h. The tube was allowed to cool to room temperature and Pd(PPh3)4 (8.1 mg, 0.007 mmol), K3PO4 (112 mg, 0.528 mmol), PhI (72.7 mg, 0.356 mmol), and DME (2 mL) were added. A GC-trace of the reaction mixture revealed PhBPin in 85.7% yield. Three freeze-pump-thaw cycles were performed to remove residual O2 and the reaction mixture was heated at 80° C. for 2 days. GC analysis showed biphenyl (81.8% GC-yield), iodobenzene (7.9.7% GC-conversion), and PhBPin (79.1% GC-conversion).

Workup

  1. customClosed system
  2. customThe tube was sealed
  3. customremoved from the box
  4. temperatureto cool to room temperature
  5. customto remove residual O2
  6. temperaturethe reaction mixture was heated at 80° C. for 2 days

Sources & evidence

ORD record
ord-ba935d64a9b94481b738fa748f67859d
Source dataset
uspto-grants-2008_02
Patent number
US07329769B2

Reaction notes

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