Tris(1,1-dimethylethyl)phosphine → 12,12-Dimethyl-10-[1,1';3',1'']terphenyl-5'-yl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275931노트

반응식

HRID 2275931 반응식
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.Br[C:24]1[CH:25]=[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:29]=1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC1C=CC(C)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[N:13]([C:24]4[CH:29]=[C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:27]=[C:26]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:25]=4)[C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4

참가 물질

7

반응물 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 100702575'-Bromo-1,1':3',1''-terphenylHCID 23676156Sodium t-butoxideHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazole

생성물 1

HCID 6679766212,12-Dimethyl-10-[1,1';3',1'']terphenyl-5'-yl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 7809P-Xylene용매

실험 절차

30 g (106 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene, 13.3 g (114 mmol) of 5′-bromo-[1,1′;3′,1″]terphenyl and 30.5 g of NaOtBu are suspended in 1.5 l of p-xylene. 0.5 g (2.11 mmol) of Pd(OAc)2 and 1.6 ml of a 1 M tri-tert-butylphosphine solution are added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 15.8 g (31 mmol, 72%).

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 200 ml of water
  6. customsubsequently evaporated to dryness
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

출처 및 근거

ORD 기록
ord-c7b1398bf89d47c7be91646677b0a4da
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126970B2

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