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

HRID 1054731노트

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HRID 1054731 반응식
[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]

참가 물질

7

반응물 4

HCID 14496CyclobutanoneHCID 433294Lithium ChlorideHCID 450407122-Bromo-5-iodobenzonitrileHCID 178418918HCID 178418918, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cd63c9f4e3d4b2abfdef4b0df56f9ff
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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