Sodium Carbonate → 5-(Furan-2-yl)-2,3-dimethoxybenzonitrile

HRID 1798583ノート

反応式

HRID 1798583 の反応式
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>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>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 226838165-Bromo-2,3-dimethoxybenzonitrile

生成物 1

HCID 584320135-(Furan-2-yl)-2,3-dimethoxybenzonitrile収率 94%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

To a mixture of 5-bromo-2,3-dimethoxybenzonitrile (0.958 g, 4.0 mmol), 2-furylboronic acid (0.53 g, 4.7 mmol), dioxane (24 mL), H2O (8 mL) and Na2CO3 (1.1 g, 10.4 mmol) was added tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each then heated at 85° C. under argon for 16.5 hrs. After cooling to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-20% EtOAc-hexanes) provided 5-(furan-2-yl)-2,3-dimethoxybenzonitrile as a white solid (0.85 g, 94% yield).

後処理

  1. customThe mixture was degassed
  2. waitby alternately putting under house vacuum and argon three times for several minutes
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with H2O
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography (0-20% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-a8494120c12d47ceaeb06de25e701b57
出典データセット
uspto-grants-2013_01
特許番号
US08343970B2

反応ノート

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