Potassium Iodide → 6,13-Bis(4-butylphenyl)pentacene

HRID 1993150

반응식

HRID 1993150 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Mg].[CH:13]1[C:34]2[C:17](=[CH:18][C:19]3[C:20](=O)[C:21]4[C:30](C(=O)[C:32]=3[CH:33]=2)=[CH:29]C2[C:23](=[CH:24][CH:25]=CC=2)[CH:22]=4)[CH:16]=[CH:15][CH:14]=1.[I-].[K+]>O1CCCC1.C(O)(=O)C>[CH2:25]([C:24]1[CH:23]=[CH:22][C:21]([C:20]2[C:7]3[C:2](=[CH:3][C:4]4[C:5]([CH:6]=3)=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:13]([C:34]3[CH:33]=[CH:32][C:19]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:17]=3)=[C:18]3[C:19]=2[CH:32]=[C:33]2[C:34](=[CH:17]3)[CH:13]=[CH:14][CH:15]=[CH:16]2)=[CH:30][CH:29]=1)[CH2:16][CH2:15][CH3:14]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 764156,13-PentacenequinoneHCID 5210591-Bromo-4-butylbenzeneHCID 5462224Magnesium

생성물 1

HCID 220134936,13-Bis(4-butylphenyl)pentacene수율 94.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
60 °C

실험 절차

6,13-bis(4-butylphenyl)pentacene was synthesized as follows. A solution of 1-bromo-4-butylbenzene (about 5.09 grams, about 32.40 mmol) in about 20 milliliters of anhydrous tetrahydrofuran (THF) was added over a period of about 1 hour to a stirred suspension of magnesium turnings (about 0.79 grams, about 32.40 mmol) in about 10 milliliters of THF in a 250 milliliter round-bottomed flask under an inert argon atmosphere. The resultant mixture was stirred at about 60° C. for about 2 hours. A solution of 6,13-pentacenequinone (about 1.0 grams, about 3.24 mmol) in about 20 milliliters of THF was added and the resulting mixture was stirred at about 60° C. for about 2 hours. Subsequently, the reaction mixture was cooled to about 22° C. to about 25° C. and quenched with ice. The reaction mixture was extracted with toluene and the organic layer was separated and dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed and a solution of potassium iodide (KI) (about 2.00 grams, about 12.0 mmol) in about 50 milliliters acetic acid (AcOH) was added to the solid residue. The resultant mixture was then refluxed for about 1 hour and then cooled to about 22° C. to about 25° C. A purple precipitate, obtained after filtration, was washed with water and methanol, yielding about 0.83 grams of 6,13-bis(4-butylphenyl)pentacene as a dark purple solid (about 47% yield). Further purification was conducted by sublimation. An overview of this process is set forth below in Scheme 1.

후처리

  1. custom6,13-bis(4-butylphenyl)pentacene was synthesized
  2. temperatureSubsequently, the reaction mixture was cooled to about 22° C. to about 25° C.
  3. customquenched with ice
  4. extractionThe reaction mixture was extracted with toluene
  5. customthe organic layer was separated
  6. dry with materialdried with anhydrous magnesium sulfate (MgSO4)
  7. customThe solvent was removed
  8. temperaturecooled to about 22° C. to about 25° C
  9. customA purple precipitate, obtained
  10. filtrationafter filtration
  11. washwas washed with water and methanol

출처 및 근거

ORD 기록
ord-ebfb86f0baf944caae83b45c8ef7f5e5
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07651885B2

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