2'-Bromoacetophenone → 1-(2-Vinylphenyl)ethanone

HRID 1011570

反応式

HRID 1011570 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C(=O)([O-])O.[Na+].[CH:16](B1OC(C)(C)C(C)(C)O1)=[CH2:17]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9])=[CH2:17]

参加物

7

反応物 3

HCID 750602'-BromoacetophenoneHCID 516892Sodium BicarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 2205361-(2-Vinylphenyl)ethanone収率 69%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

A solution of 2′-bromoacetophenone (1.6 mL, 12 mmol), sodium hydrogencarbonate (2.5 g, 30 mmol), vinylboronic acid pinacol ester (3.0 mL, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69 g, 0.60 mmol) in a mixed solvent (50 mL), which consists of water and 1,4-dioxane (1:4), was stirred at 95° C. for 2.5 hours. Water (100 mL) was added to the reaction solution and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate. After the organic layer was filtered with celite and the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (1.2 g) as an orange oil (Yield 69%).

後処理

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the organic layer was filtered with celite
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2c0d823e861149d7b49a2c42d8dc5305
出典データセット
uspto-grants-2011_07
特許番号
US07977371B2

関連ノート

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