Phenylacetylene → Thiophene, 2-(phenylethynyl)-

HRID 274423Notes

Reaction equation

HRID 274423 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]1([C:13]#[CH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:14]#[C:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 138512-Bromothiophene

Product 1

HCID 1238176Thiophene, 2-(phenylethynyl)-Yield 57.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

1 g (0.00142 mol) of bis-(triphenylphosphine)palladium chloride, 5 g (0.0262 mol) of copper iodide and 8.5 g (0.0324 mol) of triphenylphosphine were added in succesion to a solution of 163 g (1 mol) of 2-bromothiophene and 127.5 g (1.25 mol) of phenylacetylene in 850 ml of triethylamine at 25° C. Stirring was carried out for twelve hours under a nitrogen atmosphere at 80° C., after which the mixture was filtered and the filtrate was evaporated down under reduced pressure. 600 ml of methylene chloride were added to the residue and the solution was washed with three times 200 ml of water, dried over Na2SO4 and evaporated down under reduced pressure, after which 200 ml of n-pentane were added. The crystals thus obtained were filtered off under suction and dried. 106 g (57.6% of theory) of 1-(2-thienyl)-2-phenylacetylene were obtained as pale yellow crystals of melting point 49°-59 ° C. (Active Ingredient Example 1.001).

Workup

  1. waitwas carried out for twelve hours under a nitrogen atmosphere at 80° C.
  2. filtrationafter which the mixture was filtered
  3. customthe filtrate was evaporated down under reduced pressure
  4. addition600 ml of methylene chloride were added to the residue
  5. washthe solution was washed with three times 200 ml of water
  6. dry with materialdried over Na2SO4
  7. customevaporated down under reduced pressure
  8. additionafter which 200 ml of n-pentane were added
  9. customThe crystals thus obtained
  10. filtrationwere filtered off under suction
  11. customdried

Sources & evidence

ORD record
ord-69351cee38124d8aae27462d77cabe0b
Source dataset
uspto-grants-1995_02
Patent number
US05389656

Reaction notes

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