Perfluorocyclopentene → 3,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(2,5-bis(4-(tert-butyl)phenyl)thiophene)

HRID 708307

반응식

HRID 708307 반응식
Br[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=1.[F:27][C:28]1([F:39])[C:32](F)=[C:31](F)[C:30]([F:36])([F:35])[C:29]1([F:38])[F:37]>C1COCC1.CCOCC>[F:27][C:28]1([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([CH3:15])([CH3:14])[CH3:16])=[CH:11][CH:12]=3)[S:4][C:3]=2[C:17]2[CH:18]=[CH:19][C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:21][CH:22]=2)=[C:32]1[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:17]1[CH:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 11212PerfluorocyclopenteneHCID 679735833-Bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene

생성물 1

HCID 596155663,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(2,5-bis(4-(tert-butyl)phenyl)thiophene)

시약·촉매·용매 1

HCID 21868444Ether tetrahydrofuran용매

실험 절차

A solution of (30) in anhydrous THF/ether cooled to −45° C. and treated with nBu—Li-(2.5 M in hexanes, 35 mL, 87 mmol) dropwise under a n argon atmosphere. The reaction mixture was stirred for a further 15 minutes followed by addition of octafluorocyclopentene (5.6 mL, 41.5 mmol) using a cooled gas tight syringe. The reaction was allowed to stir until the temperature reached −10° C., quenched by the addition of 10% HCl (50 mL). The aqueous layer was separated and extracted with ether. The organic phases were separated and pooled, dried over MgSO4, filtered and solvent removed by rotary evaporation. The crude product was stirred in MeOH for 3 hours, and the resulting precipitate filtered, dried and purified using flash chromatography (hexanes), affording 2 fractions—F1 was pure S006 (TLC), F2 contained S006 along with a fluorescent byproduct by TLC. F1, 5.35 g, 14.8%) and F2, 10.4 g (˜75% pure, 22%) as light yellow, powdery solids. 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J=8.5 Hz, 4H), 7.30 (d, J=8.5 Hz, 4H), 7.05 (d, J=8.4 Hz, 4H), 6.92 (d, J=8.4 Hz, 4H), 6.13 (s, 2H), 1.34 (s, 18H), 0.91 (s, 18H).

후처리

  1. stirringto stir until the temperature
  2. customreached −10° C.
  3. customquenched by the addition of 10% HCl (50 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with ether
  6. customThe organic phases were separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customsolvent removed by rotary evaporation
  10. stirringThe crude product was stirred in MeOH for 3 hours
  11. filtrationthe resulting precipitate filtered
  12. customdried
  13. custompurified
  14. customaffording 2 fractions—F1

출처 및 근거

ORD 기록
ord-3a2835cccfc6448b9dc985acb4e8224f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09176357B2

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