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 2275931ノート

反応式

HRID 2275931 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 7809P-Xylene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c7b1398bf89d47c7be91646677b0a4da
出典データセット
uspto-grants-2015_09
特許番号
US09126970B2

反応ノート

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