Iodine → 1,2,4,5-Tetra-p-biphenylylbenzene

HRID 1358153

反応式

HRID 1358153 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.II.Br[C:17]1[C:22](Br)=[C:21](Br)[C:20](Br)=[C:19](Br)[C:18]=1Br>C1COCC1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:17]1[CH:22]=[C:21]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[C:20]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[CH:19][C:18]=1[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 807IodineHCID 6905HexabromobenzeneHCID 71014-Bromobiphenyl2 回

生成物 1

HCID 597890641,2,4,5-Tetra-p-biphenylylbenzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Dry Mg turnings (3.9 g, 0.16 mol) and 30 mL of anhydrous THF were added to a 1 L 3-necked round-bottomed flask equipped with a condenser, a nitrogen inlet, an additional funnel and a magnetic stirring bar. 4-Bromobiphenyl (37.2 g, 0.16 mol) was dissolved in 150 mL of THF and placed in an additional funnel. The reaction flask was placed in a 50° C. oil bath and one crystal of iodine was added. Once the reaction started 4-bromobiphenyl was added dropwise to the reaction. After addition, the brownish reaction was heated at reflux for another hour and then cooled to room temperature. A suspension of hexabromobenzene (11.0 g, 0.02 mol) in 150 mL of THF was added dropwise from an additional funnel to the reaction and the mixture was stirred at room temperature overnight. The reaction was quenched with ice and 8% hydrochloric acid and extracted with 400 mL of methylene chloride. The organic layer was washed with saturated sodium chloride solution and dried over magnesium sulfate. Solvent was evaporated and the crude product was washed with hexane and filtered to give pure product.

後処理

  1. customequipped with a condenser, a nitrogen inlet, an additional funnel and a magnetic stirring bar
  2. customplaced in an additional funnel
  3. customwas placed in a 50° C.
  4. additionwas added dropwise to the reaction
  5. additionAfter addition
  6. customthe brownish reaction
  7. temperaturewas heated
  8. temperatureat reflux for another hour
  9. additionwas added dropwise from an additional funnel to the reaction
  10. customThe reaction was quenched with ice and 8% hydrochloric acid
  11. extractionextracted with 400 mL of methylene chloride
  12. washThe organic layer was washed with saturated sodium chloride solution
  13. dry with materialdried over magnesium sulfate
  14. customSolvent was evaporated
  15. washthe crude product was washed with hexane
  16. filtrationfiltered
  17. customto give pure product

出典と根拠

ORDレコード
ord-8993d1308b6e449ebbe48a39452691fa
出典データセット
uspto-grants-2003_07
特許番号
US06596415B2

関連ノート

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