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

HRID 344013
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HRID 344013 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

13

반응물 5

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

생성물 1

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

시약·촉매·용매 7

HCID 11776
Triphenylphosphine
촉매
HCID 23938Palladium촉매
HCID 83717Copper iodide촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 887Methanol용매
HCID 1140Toluene용매
HCID 6344Dichloromethane용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-42e72b750fbd43f89b312902fb70df18
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05864050

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