Potassium Carbonate → (5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

HRID 81741

反応式

HRID 81741 の反応式
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][C:22]#[N:23]>CN(C)C=O.O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:21][C:22]#[N:23]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 69356IodoacetonitrileHCID 595986545-Bromo-2-isopropyl-4-methoxy-phenol

生成物 1

HCID 59598690(5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile収率 63.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 5-bromo-2-isopropyl-4-methoxy-phenol from step 4 (0.831 g, 3.4 mmol) and K2CO3 (0.562 g, 4.1 mmol) in 17 mL dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60° C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in 50 mL of H2O and extracted with 1:1 toluene/ethyl acetate, washed with H2O and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2Cl2) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.611 g, 63%) as a while solid.

後処理

  1. temperatureto cool to room temperature
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionextracted with 1:1 toluene/ethyl acetate
  4. washwashed with H2O
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude solid
  9. customPurification via flash chromatography (1:1 hexane/CH2Cl2)

出典と根拠

ORDレコード
ord-f36638fc0db549a89ebf1cd613d71525
出典データセット
uspto-grants-2014_09
特許番号
US08846705B2

関連ノート

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