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Potassium Phosphate, Tribasic → 1-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

HRID 2371241
ノート
印刷プレビュー

反応式

HRID 2371241 の反応式
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:45]1[C:62]2[C:61]3[C:60]4[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=4[CH:54]=[CH:53][C:52]=3[CH:51]=[C:50](B(O)O)[C:49]=2[CH:48]=[CH:47][CH:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[C:42]([C:48]3[C:49]4[CH:50]=[CH:51][C:52]5[CH:53]=[CH:54][C:55]6[CH:56]=[CH:57][CH:58]=[CH:59][C:60]=6[C:61]=5[C:62]=4[CH:45]=[CH:46][CH:47]=3)[CH:41]=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleHCID 59622711Benzo[c]phenanthren-5-ylboronic acid

生成物 1

HCID 866595461-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

試薬・触媒・溶媒 4

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 312751,4-Dioxane溶媒

実験手順

913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a vigorously stirred suspension of 17.5 g (50 mmol) of 1-phenyl-2-(4-bromophenyl)benzimidazole, 14.9 g (55 mmol) of benzo[c]phenanthrene-5-boronic acid and 25.5 g (120 mmol) of tripotassium phosphate in a mixture of 300 ml of toluene, 100 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After the mixture has been cooled, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and recrystallised three times from DMF (about 7 ml/g). Yield: 16.8 g (34 mmol), 67.8%, purity 99.9% (HPLC).

後処理

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter the mixture has been cooled
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 7 ml/g)

出典と根拠

ORDレコード
ord-005daff99dc74fc7bd2c56d5a2f89346
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08710284B2

反応ノート

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