9-Bromophenanthrene → 9-(Triethoxygermyl)phenanthrene

HRID 716589

반응식

HRID 716589 반응식
[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]

참가 물질

5

반응물 3

HCID 113099-BromophenanthreneHCID 5462224MagnesiumHCID 16684444HCID 16684444, 화합물

생성물 1

HCID 892877369-(Triethoxygermyl)phenanthrene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b0aed026cdf74621ac5d5e4fd3ad69d1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09190616B2

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