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

HRID 1252359ノート

反応式

HRID 1252359 の反応式
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]

参加物

9

反応物 4

HCID 6325Ethylene2 回HCID 80271Tri-o-tolylphosphineHCID 117898682-Bromobicyclo[4.2.0]octa-1,3,5-triene2 回HCID 713412822-Ethenylbicyclo[4.2.0]octa-1,3,5-triene

生成物 2

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-08faefba7750412dbd2f4cbd4df33ab8
出典データセット
uspto-grants-1988_05
特許番号
US04743399

反応ノート

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