Pyridine → 2,2'-Dimethylbiphenyl

HRID 1493108Notes

Reaction equation

HRID 1493108 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:8]=1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33].C([Mg]Cl)(C)(C)C>[Ni](Br)Br.O1CCCC1>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 72382-ChlorotolueneHCID 11776TriphenylphosphineHCID 178418310HCID 178418310, compound

Product 1

HCID 117972,2'-Dimethylbiphenyl

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a nitrogen purged three-neck 100 mL flask was added nickel(II) bromide (0.22 grams, 1 mmole), polyvinyl pyridine (0.63 grams of Reillex® 402 obtained from Reilly Tar and Chemical Company, Indianapolis, IN), triphenylphosphine (2.62 grams, 10 mmole), 2-chlorotoluene (2.53 grams 20 mmole) and tetrahydrofuran (20 mL). The mixture was stirred at room temperature for 5 minutes and then tertiary-butyl-magnesium chloride (12 mL of 2.0 Molar solution in THF, 24 mmole) was added dropwise over a 10 minute period. The reaction warmed upon addition and at the end of the addition was heated to reflux for 14 hours. The mixture was cooled to ambient and analyzed by conventional gas chromatographic methods. The results of the reaction are:

Workup

  1. customobtained from Reilly Tar and Chemical Company, Indianapolis
  2. temperatureThe reaction warmed upon addition and at the end of the addition
  3. temperaturewas heated
  4. temperatureto reflux for 14 hours
  5. temperatureThe mixture was cooled to ambient and
  6. customThe results of the reaction

Sources & evidence

ORD record
ord-bc262a482e1b40b18969640e05f67ac9
Source dataset
uspto-grants-1991_06
Patent number
US05021380

Reaction notes

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