Phenyl-1-naphthylamine → N~2~,N~7~-Di(naphthalen-1-yl)-N~2~,N~7~-diphenyl-9H-fluorene-2,7-diamine

HRID 42389

반응식

HRID 42389 반응식
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[C:16]1([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:23]1([N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([N:22]([C:23]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH:26]=[CH:25][CH:24]=5)[C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[CH:9][CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 7013Phenyl-1-naphthylamineHCID 1400732,7-Dibromofluorene

생성물 1

HCID 58262064N~2~,N~7~-Di(naphthalen-1-yl)-N~2~,N~7~-diphenyl-9H-fluorene-2,7-diamine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a 2-liter three-neck round bottom flask was added anhydrous toluene (1000 mL) by cannula. 2,7-dibromofluorene (50.0 g) was added to this flask, then stirred until all dissolved. N-phenyl-1-naphthylamine (81.14 g) was then added. The reaction vessel was purged with a strong nitrogen flow for 30 minutes, followed by the addition of sodium tert-butoxide (44.5 g) by funnel. Tris(dibenzylideneacetone)dipalladium(0) (5.65 g) was added to the reaction. Tri-tert-butyl phosphine (3.75 g) in anhydrous toluene (20 mL) was added via syringe. The reaction was heated to reflux for 2 hours and reaction completion was confirmed by thin-layer chromatography. The vessel was removed from heat and allowed to cool to room temperature. The reaction solution was filtered through a celite/silica gel plug and solvent was then removed by rotary evaporation. The crude material was initially purified by flash chromatography, followed by sublimation to yield NMR pure product.

후처리

  1. customThe reaction vessel was purged with a strong nitrogen flow for 30 minutes
  2. additionfollowed by the addition of sodium tert-butoxide (44.5 g) by funnel
  3. additionTris(dibenzylideneacetone)dipalladium(0) (5.65 g) was added to the reaction
  4. additionTri-tert-butyl phosphine (3.75 g) in anhydrous toluene (20 mL) was added via syringe
  5. temperatureThe reaction was heated
  6. temperatureto reflux for 2 hours
  7. customreaction completion
  8. customThe vessel was removed
  9. temperaturefrom heat
  10. filtrationThe reaction solution was filtered through a celite/silica gel plug and solvent
  11. customwas then removed by rotary evaporation
  12. customThe crude material was initially purified by flash chromatography
  13. customto yield NMR pure product

출처 및 근거

ORD 기록
ord-0143c30e3114437fa25f8ee57f76bfc1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08535974B2

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