Cesium carbonate → 1-Cyclopropyl-3,5-dimethoxybenzene

HRID 41251ノート

反応式

HRID 41251 の反応式
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C1(P(C2CCCCC2)[C:19]2C=CC=C[C:20]=2[C:25]2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:25]1([C:2]2[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=2)[CH2:20][CH2:19]1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

生成物 1

HCID 582233921-Cyclopropyl-3,5-dimethoxybenzene収率 490.8%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1-bromo-3,5-dimethoxybenzene (2.00 g, 9.21 mmol) in dioxane (30 mL) and water (10 mL) were added potassium cyclopropyl trifluoroborate (2.73 g, 18.4 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (756 mg, 1.84 mmol), palladium(II) acetate (207 mg, 0.92 mmol) and cesium carbonate (18.0 g, 55.3 mmol), and the mixture was heated at 100° C. for 16 hours. After the reaction was completed, water was added to the reaction mixture, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1) to obtain the title compound (1.61 g, 9.03 mmol).

後処理

  1. extractionwas extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1)

出典と根拠

ORDレコード
ord-1febc6efb69144cd885e0f3d583c497d
出典データセット
uspto-grants-2013_09
特許番号
US08530504B2

反応ノート

読み込み中…