Cyclobutanone → 2-Bromo-5-(1-hydroxycyclobutyl)benzonitrile

HRID 1054731ノート

反応式

HRID 1054731 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].C([Mg]Cl)(C)C.[Cl-].[Li+].[C:18]1(=[O:22])[CH2:21][CH2:20][CH2:19]1>O1CCCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:18]2([OH:22])[CH2:21][CH2:20][CH2:19]2)=[CH:6][C:3]=1[C:4]#[N:5]

参加物

7

反応物 4

HCID 14496CyclobutanoneHCID 433294Lithium ChlorideHCID 450407122-Bromo-5-iodobenzonitrileHCID 178418918HCID 178418918、化合物

生成物 1

HCID 866987292-Bromo-5-(1-hydroxycyclobutyl)benzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

To 2-bromo-5-iodobenzonitrile (1457 mg, 4.730 mmol) in tetrahydrofuran (10 mL) at −40° C. was added isopropyl magnesium chloride.lithium chloride (1.3 M in THF, 4.4 mL, 5.7 mmol) dropwise. The mixture was stirred at −40° C. for 10 minutes, and was then treated with cyclobutanone (0.4 mL, 5.2 mmol) dropwise at −40° C. The reaction mixture was warmed to room temperature and stirred at that temperature for 16 hours. The reaction mixture was poured into water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound which was used directly in the next step without further purification.

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred at that temperature for 16 hours
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1cd63c9f4e3d4b2abfdef4b0df56f9ff
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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