Dimethylformamide → 2-Bromo-9,9-dimethoxyethylfluorene

HRID 720018

반응식

HRID 720018 반응식
[Br:1][C:2]1C=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH3:15][C:16]([CH3:19])([O-:18])C.[K+].BrC[CH2:23][O:24]C.[CH3:26]N(C)C=O>O>[Br:1][CH2:2][CH2:3][C:4]1[C:15]2[C:16]([O:24][CH3:23])([O:18][CH3:26])[C:19]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 143362-Bromo-9H-fluoreneHCID 809722-Bromoethyl methyl ether2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 695870882-Bromo-9,9-dimethoxyethylfluorene

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

To a solution of 2-bromofluorene (2.0 g, 8.2 mmol) in dimethylformamide (dry, 30 ml) was added potassium t-butoxide (2.74 g, 24.4 mmol), giving a deep orange in color. The mixture was stirred at 45° C. for 20 min and added 2-bromoethylmethyl ether (3.5 g, 2.5 mmol) dropwise. Stirring was continued at the same temperature for overnight to give an orange solution. Another portion of 2-bromoethylmethyl ether (1.4 g, 1.0 mmol) was added and the mixture stirred at 80° C. for 4 h. It was diluted with water (100 ml). The products extracted with ethylacetate (20 ml) and washed with water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product. It was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent) to give 2-bromo-9,9-dimethoxyethylfluorene (1.5 g).

후처리

  1. customgiving a deep orange in color
  2. stirringStirring
  3. waitwas continued at the same temperature for overnight
  4. customto give an orange solution
  5. stirringthe mixture stirred at 80° C. for 4 h
  6. extractionThe products extracted with ethylacetate (20 ml)
  7. washwashed with water
  8. dry with materialOrganic layer was dried over magnesium sulfate
  9. concentrationconcentrated in vacuuo
  10. customto afford the crude product
  11. customIt was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent)

출처 및 근거

ORD 기록
ord-dc989689314d4eefbdcd9bd4ab551516
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132572B2

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