Ethylene → 7-Ethenylbicyclo[4.2.0]octa-1,3,5-triene

HRID 1252359노트

반응식

HRID 1252359 반응식
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]2[CH2:5][CH2:6][C:3]=12.[CH:10]([C:12]1[CH:19]=[CH:18][CH:17]=[C:14]2[CH2:15][CH2:16][C:13]=12)=[CH2:11].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C=C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C.C(#N)C>[CH:10]([CH:5]1[C:4]2=[CH:7][CH:8]=[CH:9][CH:2]=[C:3]2[CH2:6]1)=[CH2:11].[CH:10]([C:12]1[CH:19]=[CH:18][CH:17]=[C:14]2[CH2:15][CH2:16][C:13]=12)=[CH2:11]

참가 물질

9

반응물 4

HCID 6325Ethylene2회HCID 80271Tri-o-tolylphosphineHCID 117898682-Bromobicyclo[4.2.0]octa-1,3,5-triene2회HCID 713412822-Ethenylbicyclo[4.2.0]octa-1,3,5-triene

생성물 2

HCID 27530077-Ethenylbicyclo[4.2.0]octa-1,3,5-trieneHCID 713412822-Ethenylbicyclo[4.2.0]octa-1,3,5-triene

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

반응 조건

온도
125 °C

실험 절차

The monomer is prepared by heating a mixture of 4-bromobenzocyclobutene with 4-vinylbenzocyclobutene at reflux. Vinylbenzocyclobutene is prepared by adding 0.98 g of 4-bromobenzocyclobutene, 0.04 g palladium (II) acetate, and 0.17 g of tri-o-tolylphosphine to a mixture of 100 ml acetonitrile and 0.6 g of triethylamine in a 450 ml Parr pressure reactor. The reactor is pressurized with 250 psig ethylene. The mixture is heated to 125° C. and stirred for 16 hours. The apparatus is cooled and the remaining ethylene is vented. The product is washed with water and 5 percent hydrochloric acid and dried over MgSO4. The solvent is removed to provide 4-vinylbenzocyclobutene. A 2.4 g sample of 4-bromobenzocyclobutene, a 1.7 g of 4-vinylbenzocyclobutene, a 2.4 g of tri-n-butylamine, a 100 mg of tri-o-tolylphosphine, 29 mg palladium (II) acetate and 10 ml acetonitrile are added to a fask equipped with a reflux condenser, nitrogen inlet, and magnetic stirrer. The reaction mixture is heated to reflux under nitrogen for 4 hours. The solution is cooled to room temperature and stirred into 60 ml of 10 percent hydrochloric acid solution. The precipitate is collected by filtration, washed with water and air dried. The product is recrystallized from ethylacetate and has a melting point of 132° to 133° C.

후처리

  1. customThe monomer is prepared
  2. temperatureby heating
  3. temperatureat reflux
  4. temperatureThe apparatus is cooled
  5. washThe product is washed with water and 5 percent hydrochloric acid
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed

출처 및 근거

ORD 기록
ord-08faefba7750412dbd2f4cbd4df33ab8
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743399

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