3-Bromotoluene → 3'-Methyl[1,1'-biphenyl]-3-carbonitrile

HRID 1700280Notes

Reaction equation

HRID 1700280 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=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.O1CCOCC1>[C:5]([C:4]1[CH:3]=[C:2]([C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

5

Reactant 2

HCID 115603-BromotolueneHCID 233813-Bromobenzonitrile

Product 1

HCID 13939753'-Methyl[1,1'-biphenyl]-3-carbonitrileYield 66.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromobenzonitrile (910 mg), Pd(Ph3P)4 (290 mg), (Me3Sn)2 (1.64 g) and dioxane (20 mL) was sealed under argon in a pressure tube. The tube was then heated at 100-110° C. for 3 hours with stirring and another 15 hours at 80° C. To the reaction mixture was added 1-bromo-3-methylbenzene (940 mg), Pd(PPh3)4 (290 mg) and dioxane (5 mL) under argon. The sealed tube was heated at 135-140° C. with stirring for two days. The catalyst was filtered off and the filtrate was poured into water and extracted with ethyl acetate (3×). The organic layer was washed with brine, dried over Mg2SO4, concentrated and purified on silica gel column (ethyl acetate/hexane, 1:3) to afford 0.64 g of 3-(3-cyanophenyl)-1-methylbenzene.

Workup

  1. customwas sealed under argon in a pressure tube
  2. temperatureThe sealed tube was heated at 135-140° C.
  3. stirringwith stirring for two days
  4. filtrationThe catalyst was filtered off
  5. additionthe filtrate was poured into water
  6. extractionextracted with ethyl acetate (3×)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Mg2SO4
  9. concentrationconcentrated
  10. custompurified on silica gel column (ethyl acetate/hexane, 1:3)

Sources & evidence

ORD record
ord-7e7471371ef84ed6b5916003de8fd24f
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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