9-Bromophenanthrene → 9-(Triethoxygermyl)phenanthrene

HRID 716589

反応式

HRID 716589 の反応式
[Mg].C(O[Ge:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])C.Br[C:16]1[C:17]2[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[CH:29]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2>C1COCC1>[CH2:13]([O:12][Ge:5]([O:6][CH2:7][CH3:8])([O:9][CH2:10][CH3:11])[C:16]1[C:17]2[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[CH:29]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:14]

参加物

5

反応物 3

HCID 113099-BromophenanthreneHCID 5462224MagnesiumHCID 16684444HCID 16684444、化合物

生成物 1

HCID 892877369-(Triethoxygermyl)phenanthrene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 3-neck 500 mL flask was filled with magnesium turnings (8 g), THF (100 g) and tetraethoxygermane (35 g), and heated to reflux. 9-Bromophenanthrene (30 g) was added to the flask in small portions. Grignard started after a few minutes and kept refluxing by its own heat for ten minutes. The reaction was allowed to cool for 1 hour, after which magnesium salts were precipitated with heptanes (300 mL). The solution was filtered, followed by evaporation of volatiles by rotary evaporator. The material was distilled three times at <1 mbar, giving colorless 9-(triethoxygermyl)phenanthrene (bp. 170 . . . 190° C., 21 g, 46.7% overall yield based on 2-bromophenanthrene, purity 99.5% by GC/MS).

後処理

  1. temperatureheated to reflux
  2. waitGrignard started after a few minutes
  3. temperaturekept refluxing by its
  4. temperatureown heat for ten minutes
  5. temperatureto cool for 1 hour
  6. customafter which magnesium salts were precipitated with heptanes (300 mL)
  7. filtrationThe solution was filtered
  8. customfollowed by evaporation of volatiles by rotary evaporator
  9. distillationThe material was distilled three times at <1 mbar

出典と根拠

ORDレコード
ord-b0aed026cdf74621ac5d5e4fd3ad69d1
出典データセット
uspto-grants-2015_11
特許番号
US09190616B2

関連ノート

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