Phenylacetylene → HCID 59992763, compound

HRID 1365587Notes

Reaction equation

HRID 1365587 reaction equation
Br[C:2]1[C:19]2[C:10](=[CH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:39]1([C:45]#[CH:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Al]>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.C(N(CC)CC)C>[C:39]1([C:45]#[C:46][C:9]2[C:10]3[C:19](=[CH:18][C:17]4[C:12]([CH:11]=3)=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:2]=[C:3]3[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]3)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

8

Reactant 4

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 5359268AluminumHCID 713579985-Bromotetracene2×

Product 1

HCID 59992763HCID 59992763, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

5-Bromonaphthacene (1.00 g, 3.26 mmol, prepared as described in Example 1, Step 1), 31 mg of copper(I) iodide (0.163 mmol), 85 mg of triphenylphosphine (0.33 mmol) and 114 mg of dichlorobis(triphenylphosphine)palladium(II) catalyst (0.163 mmol) were added to an oven-dried glass pressure tube equipped with a magnetic stirrer. Dry triethylamine (20 ml) was added and the mixture was degassed with nitrogen for 15 minutes. Phenylacetylene (0.5 g, 0.46 ml, 4.88 mmol) was then added by syringe. The tube was sealed and heated in an oil bath to 95° C. while covered with aluminum foil to exclude light (for the duration of the reaction and work up, exposure to light was minimized). The reaction mixture was heated for two hours, and then allowed to cool slowly. The tube contents were dark red with a white precipitate. Upon further cooling, a dark red precipitate formed. TLC analysis with 30% dichloromethane/hexanes showed that all 5-bromonaphthacene had been consumed.

Workup

  1. customequipped with a magnetic stirrer
  2. customthe mixture was degassed with nitrogen for 15 minutes
  3. customThe tube was sealed
  4. customfor the duration of the reaction
  5. temperatureThe reaction mixture was heated for two hours
  6. temperatureto cool slowly
  7. customUpon further cooling, a dark red precipitate formed
  8. customhad been consumed

Sources & evidence

ORD record
ord-388e019ab70349b2a354ea35622bdb6f
Source dataset
uspto-grants-2011_02
Patent number
US07892702B2

Reaction notes

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