Toluene → 1,3-Bis[4-(phenylethynyl)phenyl]propan-2-one

HRID 1869063Notes

Reaction equation

HRID 1869063 reaction equation
BrC1C=CC([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15](=[O:30])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2C2C=CC(Br)=CC=2)=CC=1.[CH2:31](N(CC)CC)C.[C:38]1([C:44]#[CH:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C)C=O.[C:51]1([CH3:57])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:38]1([C:44]#[C:45][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C:15](=[O:30])[CH2:14][C:9]3[CH:10]=[CH:11][C:12]([C:31]#[C:57][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:13][CH:8]=3)=[CH:22][CH:21]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

9

Reactant 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 67405464HCID 67405464, compound

Product 1

HCID 579767661,3-Bis[4-(phenylethynyl)phenyl]propan-2-one

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a 250 ml flask was placed 18.4 grams (0.05 mole) of 1,3-bis-(4-bromophenylphenyl)-2-propanone, 24 grams (0.24 mole) of triethylamine, 12 grams (0.12 mole) of phenylacetylene, and 60 milliliters of N,N-dimethylformamide. The reaction mixture was purged with nitrogen for 15 minutes then 0.60 gram (0.0023 mole) of triphenylphosphine and 0.08 gram (0.00036 mole) of palladium acetate were added. After heating the reaction mixture at 80° C. under a nitrogen atmosphere for 20 hours, the flask was allowed to cool to room temperature, then water (200 milliliters) and toluene (200 milliliters) were added. The resulting organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl then dried over anhydrous Na2SO4. The pure product (14.5 grams) was obtained upon removal of the toluene and recrystallization from toluene/hexanes in 71% isolated yield.

Workup

  1. customIn a 250 ml flask was placed
  2. customThe reaction mixture was purged with nitrogen for 15 minutes
  3. temperatureto cool to room temperature
  4. washThe resulting organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl
  5. dry with materialthen dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-7375a48fdc554d3e839ffea8fc0ca4c2
Source dataset
uspto-grants-2009_12
Patent number
US07635741B2

Reaction notes

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