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Diphenylamine → 5-(Diphenylamino)benzo[c]phenanthrene

HRID 1470908
ノート
印刷プレビュー

反応式

HRID 1470908 の反応式
ClP(C(C)(C)C)C(C)(C)C.Br[C:12]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=[CH:15][C:14]=2[CH:13]=1.[C:30]1([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:37]1([N:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:12]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH:16]=[CH:15][C:14]=3[CH:13]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11487DiphenylamineHCID 139566Di-tert-butylchlorophosphineHCID 106624825-Bromobenzo[c]phenanthreneHCID 23676156Sodium t-butoxide

生成物 1

HCID 585113625-(Diphenylamino)benzo[c]phenanthrene

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

190 μl (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.3 g (50 mmol) of 5-bromobenzo[c]phenanthrene, 10.2 g (60 mmol) of diphenylamine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. The product is purified by recrystallisation from dioxane five times (about 8 ml/g). Yield: 12.6 g (32 mmol), 64.1%, purity 99.9% (HPLC).

後処理

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 5 h
  3. customthe organic phase is separated off
  4. filtrationfiltered through silica gel
  5. customevaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol
  6. additionare then added
  7. temperatureAfter cooling
  8. filtrationthe solid is filtered off with suction
  9. customThe product is purified by recrystallisation from dioxane five times (about 8 ml/g)

出典と根拠

ORDレコード
ord-47e4575dc3a44914ac06ca59f8e0cf9e
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006503B2

反応ノート

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