Hexane → 3-[4-(2-Ethylhexyl)-phenyl]-thiophene

HRID 1175088

반응식

HRID 1175088 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:14][CH3:15])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.Br[C:28]1[CH:32]=[CH:31][S:30][CH:29]=1>[Cl-].[Cl-].[Zn+2].Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:14]([CH:9]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:3][CH:4]=1)[CH3:15]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 133833-BromothiopheneHCID 595582531-Bromo-4-(2-ethylhexyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 595582573-[4-(2-Ethylhexyl)-phenyl]-thiophene

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 178418745HCID 178418745, 화합물촉매

반응 조건

온도
-78 °C

실험 절차

A dry 250-mL three-neck round bottom flask, equipped with a condenser, was charged with 1-bromo-4-(2-ethylhexyl)-benzene (8 g, 0.03 mol) and purged with N2 followed by addition of anhydrous THF (50 mL) via a deoxygenated syringe. The reaction flask was cooled to −78° C. and n-butyllithium, a 2.5 M solution in hexane (12 mL, 0.03 mol), was added dropwise via syringe. The reaction mixture was stirred for 1 hour at −78° C. Anhydrous ZnCl2 (4.09 g, 0.03 mol) was added in one portion and completely dissolved after 30 minutes of stirring. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature, whereupon 3-bromothiophene (5.38 g, 0.03 mol) and Ni(dppp)Cl2 (0.32 g, 2 mol %) were added. The solution was heated up to reflux and maintained at that temperature for 12 hours, then cooled to ambient temperature, and quenched with cold HCl (10 mL, 1.0 N). The aqueous layer was separated and extracted with diethyl ether (3×100 mL). The organic phase was collected and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified by recrystallization from methanol affording 5.3 g (65%) of white solid.

후처리

  1. customA dry 250-mL three-neck round bottom flask, equipped with a condenser
  2. custompurged with N2
  3. additionfollowed by addition of anhydrous THF (50 mL) via a deoxygenated syringe
  4. dissolutioncompletely dissolved after 30 minutes
  5. stirringof stirring
  6. customThe cooling bath was removed
  7. additionwere added
  8. temperatureThe solution was heated up
  9. temperatureto reflux
  10. temperaturemaintained at that temperature for 12 hours
  11. temperaturecooled to ambient temperature
  12. customquenched with cold HCl (10 mL, 1.0 N)
  13. customThe aqueous layer was separated
  14. extractionextracted with diethyl ether (3×100 mL)
  15. customThe organic phase was collected
  16. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  17. filtrationAfter the product was filtered
  18. customthe solvent was removed by rotary evaporation
  19. customThe crude product was purified by recrystallization from methanol affording 5.3 g (65%) of white solid

출처 및 근거

ORD 기록
ord-b84dcdcfb2384615bcc5ae0c973a233d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838624B2

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