Phenylacetylene → 5-Nitro-2-phenylbenzofuran

HRID 1896792Notes

Reaction equation

HRID 1896792 reaction equation
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].N1CCC[C@H]1CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)#[CH:39]>[Pd].O.[Cu](I)I.C(OCC)(=O)C>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:39][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

9

Reactant 4

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 2849492-iodo-4-nitrophenolHCID 640091L-Prolinol

Product 1

HCID 111724805-Nitro-2-phenylbenzofuranYield 30%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-iodo-4-nitrophenol (500 mg, 1.89 mmol), prolinol (573 mg, 5.66 mmol), palladium on carbon (60 mg, 0.06 mmol), triphenylphosphine (59.4 mg, 0.226 mmol) and copper iodide (22 mg, 0.113 mmol) in water (6 mL) was stirred for 1 h at room temperature. Ethynylbenzene (482 mg, 4.72 mmol) was slowly added, and the resulting mixture was heated at 80° C. for 3 h. After cooling, ethyl acetate was added, and the mixture was passed through a pad of Celite®. The filtrate was washed with water; the combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting material was purified by column chromatography eluting with ethyl acetate/hexanes 1:40 v/v to afford 134 mg (30%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. washThe filtrate was washed with water
  3. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting material was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes 1:40 v/v

Sources & evidence

ORD record
ord-e8fbc4ccae0a4a47b640997407e9e41c
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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