Nitrogen → Bis[4-(3-ethynylphenoxy)phenyl]methanone

HRID 344013Notes

Reaction equation

HRID 344013 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=3)=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[CH3:31][C:32](O)(C#C)C.N#N.[OH-].[Na+].[CH2:41](N(CC)CC)[CH3:42]>[Pd].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.CO.C1(C)C=CC=CC=1.C(Cl)Cl>[C:31]([C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:41]#[CH:42])[CH:20]=3)=[CH:16][CH:17]=2)=[O:11])=[CH:26][CH:27]=1)#[CH:32]

Participants

13

Reactant 5

HCID 947NitrogenHCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22494465HCID 22494465, compound

Product 1

HCID 53863473Bis[4-(3-ethynylphenoxy)phenyl]methanoneYield 94%

Reagents, catalysts & solvents 7

HCID 11776TriphenylphosphineCatalystHCID 23938PalladiumCatalystHCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

In 20 ml of triethylamine, dissolved are 1.4 g (2.7 mmol) of 4,4'-bis(3-bromophenoxy)benzophenone and 0.67 g (8 mmol) of 2-methyl-3 -butyne-2-ol. Through this reaction mixture, N2 gas was allowed to flow for 20 min. To the resultant, 0.02 g of triphenylphosphine, 0.005 g of a palladium catalyst, i.e. (Ph3P)2PdCl2, and 0.005 g of copper iodide were added and reacted at 80° C. for 20 hours. The reaction mixture was then washed with water and subjected to extraction with methylenechloride. A intermediate reaction product was obtained by removal of the methylenechloride. To this intermediate reaction product, 20 ml of toluene, 10 ml of methanol, and 0.8 g of NaOH were added, and subsequently, the methanol and a portion of the toluene were distilled off at a temperature of 100° C. The resultant was then washed with water and subjected to extraction with methylenechloride. Finally, the extracting solvent was removed to obtain 1.3 g of 4,4'-bis(3-ethynylphenoxy) benzophenone. The yield was approximately 94%. The following is the reaction formula of this synthesis. ##STR8##

Workup

  1. customreacted at 80° C. for 20 hours
  2. washThe reaction mixture was then washed with water
  3. extractionsubjected to extraction with methylenechloride
  4. customA intermediate reaction product
  5. additionwere added
  6. distillationsubsequently, the methanol and a portion of the toluene were distilled off at a temperature of 100° C
  7. washThe resultant was then washed with water
  8. extractionsubjected to extraction with methylenechloride
  9. customFinally, the extracting solvent was removed

Sources & evidence

ORD record
ord-42e72b750fbd43f89b312902fb70df18
Source dataset
uspto-grants-1999_01
Patent number
US05864050

Reaction notes

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