Lithium Chloride → 2-Hydroxy-4-vinyl-benzoic acid methyl ester

HRID 629469

反応式

HRID 629469 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[CH2:13](C([Sn])=C(CCCC)CCCC)[CH2:14]CC.[Cl-].[Li+].[F-].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:12][C:4]1[CH:3]=[C:2]([CH:13]=[CH2:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

参加物

7

反応物 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 13983552Methyl 4-bromo-2-hydroxybenzoateHCID 53438229Tri(butyl)vinyltin

生成物 1

HCID 200893762-Hydroxy-4-vinyl-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of methyl 4-bromo-2-hydroxybenzoate (3.0 g) in DMF (50.0 mL) were added tributylvinyltin (6.18 g), bis(triphenylphosphine)palladium(II) chloride (0.46 g) and lithium chloride (4.07 g), and the mixture was stirred at 90° C. for 2 hr under argon atmosphere. To the reaction mixture was added aqueous potassium fluoride solution, and the precipitated insoluble substance was removed by filtration through Celite. The filtrate was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound. This compound was used in the next step without an additional purification.

後処理

  1. customthe precipitated insoluble substance was removed by filtration through Celite
  2. additionThe filtrate was diluted with ethyl acetate
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-cd2cb1927ff14a24a95582ab0dd2aba1
出典データセット
uspto-grants-2016_04
特許番号
US09315458B2

関連ノート

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