Vinyl Acetate → 1-Fluoro-2-(2-vinyloxyethyl)-benzene

HRID 20330

반응식

HRID 20330 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11](OC=C)(=O)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][CH:11]=[CH2:12]

참가 물질

6

반응물 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 27332962-(2-Fluorophenyl)ethan-1-ol

생성물 1

HCID 685635321-Fluoro-2-(2-vinyloxyethyl)-benzene수율 72.2%

시약·촉매·용매 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimer촉매HCID 1140Toluene용매

반응 조건

온도
95 °C

실험 절차

Combine 2-(2-fluorophenyl)-ethanol (3.08 g, 22.0 mmol), vinyl acetate (4 mL, 43.3 mmol), anhydrous toluene (22 mL), chloro(1,5-cyclooctadiene)iridium(I) dimer (155 mg, 0.231 mmol), and anhydrous sodium carbonate (1.5 g, 14.2 mmol) in a dry round-bottom flask fitted with a reflux condensor under a nitrogen atmosphere. Heat the resulting mixture to 95° C. for 5 hours. Cool the reaction mixture to room temperature. Vacuum filter the resultant slurry to remove inorganic precipitates, washing the collected solid with hexanes. Concentrate and purify (silica gel chromatography, eluting with hexanes) to give the title compound as a yellow oil (2.64 g, 72%).

후처리

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationVacuum filter the resultant slurry
  3. customto remove inorganic precipitates
  4. washwashing the collected solid with hexanes
  5. concentrationConcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes)

출처 및 근거

ORD 기록
ord-7b1b0cb0cdd642c8a96a6098f2f2bb17
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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