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

HRID 20330

反応式

HRID 20330 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 685635321-Fluoro-2-(2-vinyloxyethyl)-benzene収率 72.2%

試薬・触媒・溶媒 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimer触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7b1b0cb0cdd642c8a96a6098f2f2bb17
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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