p-Bromoacetophenone → 1-[4-(Phenylethynyl)phenyl]ethan-1-one

HRID 1242825Notes

Reaction equation

HRID 1242825 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CCOCC>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]#[C:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 7466p-BromoacetophenoneHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 25517Ammonium Chloride

Product 1

HCID 27793131-[4-(Phenylethynyl)phenyl]ethan-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Compound 5 (30 mg, 2 μmol Pd), 1-(4-bromo-phenyl)ethan-1-one (0.20 g, 1 mmol), phenylacetylene (0.16 g, 1.5 mmol), and triethylamine (3 mL) were sequentially added into a 15 mL septum-sealed test tube under protection of nitrogen. The mixture was then heated at 90° C. for 72 h. After it was cooled to the room temperature, 8 mL of anhydrous ether was added to precipitate compound 5. The mixture was centrifuged and the upper liquid layer was transferred via a syringe into a 20 mL round-bottom flask. Repeated the above precipitation procedure once. The combined liquid layer was concentrated under reduced pressure to give an oily residue. A saturated ammonium chloride solution (5 mL) was then added. The resulting mixture was extracted by ethyl acetate (10 mL×3), dried over anhydrous magnesium sulfate, filtrated, and concentrated to give a crude product. The crude product was further purified by column chromatography (silica gel, hexane/ethyl acetate=4/1) to give 0.21 g (98% yield) of 1-(4-acetylphenyl)-2-phenylethyne. 1H NMR (400 MHz, CDCl3) δ 2.57 (s, 3H), 7.33–7.35 (m, 3H), 7.52–7.54 (m, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.91 (d, J=8.2 Hz, 2H) ppm.

Workup

  1. customseptum-sealed test tube under protection of nitrogen
  2. additionwas added
  3. customto precipitate compound 5
  4. customthe upper liquid layer was transferred via a syringe into a 20 mL round-bottom flask
  5. customthe above precipitation procedure once
  6. concentrationThe combined liquid layer was concentrated under reduced pressure
  7. customto give an oily residue
  8. extractionThe resulting mixture was extracted by ethyl acetate (10 mL×3)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated
  12. customto give a crude product
  13. customThe crude product was further purified by column chromatography (silica gel, hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-167d56ad2f15481197855d4eda08e927
Source dataset
uspto-grants-2006_10
Patent number
US07115762B2

Reaction notes

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