Ethanol → 2-Chloro-6-ethoxybenzonitrile

HRID 1158826노트

반응식

HRID 1158826 반응식
CC[CH2:3][CH2:4][O-:5].[Na+].C(O)C.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14].C(Cl)(Cl)Cl>C1COCC1.O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:5][CH2:4][CH3:3])[C:12]=1[C:13]#[N:14]

참가 물질

7

반응물 4

HCID 702EthanolHCID 6212ChloroformHCID 695872-Chloro-6-fluorobenzonitrileHCID 23669364Sodium n-butylate

생성물 1

HCID 222709292-Chloro-6-ethoxybenzonitrile수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of sodium 1-butoxide (65 g, 0.642 mol) in THF (1 L), at room temperature under a dry nitrogen atmosphere, ethanol (250 mL, 5.35 mol) was added over a 10 minute period. To the resulting solution, 2-chloro-6-fluorobenzonitrile (100 g, 0.642 mol) was added in portions. The reaction mixture was stirred at room temperature for 30 minutes and then reduced to a volume of approximately 250 mL under reduced pressure. The resulting mixture was poured into chloroform and water and the layers separated. The organic layer was washed with water (twice) and brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to afford a light yellow solid. This material was recrystallized from hexanes to provide the 2-chloro-6-ethoxybenzonitrile, 135, (101 g, 87% yield) as a white crystalline solid.

후처리

  1. customthe layers separated
  2. washThe organic layer was washed with water (twice) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto afford a light yellow solid
  7. customThis material was recrystallized from hexanes

출처 및 근거

ORD 기록
ord-d43f8b5cf77542039d4ba795f215839f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812038B2

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