Chlorodimethylphosphine → 9-Dimethylphosphinofluorene

HRID 431177노트

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HRID 431177 반응식
Cl[P:2]([CH3:4])[CH3:3].[C:5]1([Li])[C:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1>CCCCC>[CH3:3][P:2]([CH3:4])[CH:16]1[C:17]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2

참가 물질

4

반응물 2

HCID 69936Chlorodimethylphosphine2회HCID 178506660HCID 178506660, 화합물

생성물 1

HCID 187635119-Dimethylphosphinofluorene수율 99.6%

시약·촉매·용매 1

HCID 8003Pentane용매2회

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온도
-70 °C

실험 절차

A solution of chlorodimethylphosphine, ClPMe2, (1.0 g, 10.39 mmol) in 20 ml of pentane was added at −70° C. over 10 min through a cannula to a suspension of fluorenyllithium, (C13H9)Li, (1.788 g, 10.39 mmol) in 30 ml of dry pentane. After brief stirring at −70° C., the cooling bath was removed and the mixture was stirred for 4 hours at room temperature under an Ar atmosphere (with occasional heating by means of a hairdryer). 20 ml of toluene were added to the suspension to assist the dissolution of the product. The pale yellow suspension was filtered and volatile components were removed from the filtrate under vacuum to leave 2.34 g (99.6%) of 9-dimethylphosphinofluorene in the form of a pale yellow oil, which is pure according to 1H and 31P NMR. The product, 9-dimethylphosphinofluorene, (2.34 g, 10.34 mmol) was diluted in 25 ml of pentane and cooled to −70° C. BuLi (4.20 ml of a 2.5 molar solution, 10.5 mmol) was added to the cooled solution and the mixture was stirred briefly at −70° C. and then at room temperature. The clear yellow solution slowly becomes turbid at room temperature and a yellow precipitate begins to form. After a reaction time of 5 hours at room temperature, the mixture was filtered through a cannula and the yellow solid was washed with dry pentane (3×5 ml) and dried under high vacuum to leave 1.91 g (80%) of a loose orange-yellow solid, which is the title compound, 9-dimethylphosphinofluorenyllithium, according to 1H and 31P NMR spectroscopy.

후처리

  1. customthe cooling bath was removed
  2. stirringthe mixture was stirred for 4 hours at room temperature under an Ar atmosphere (
  3. temperaturewith occasional heating by means of a hairdryer)
  4. addition20 ml of toluene were added to the suspension
  5. dissolutionthe dissolution of the product
  6. filtrationThe pale yellow suspension was filtered
  7. customvolatile components were removed from the filtrate under vacuum

출처 및 근거

ORD 기록
ord-65cd9b3d90954bff97e412208b02f7ce
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06657027B2

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