Ethanol → 2-Chloro-6-ethoxybenzonitrile

HRID 1158826ノート

反応式

HRID 1158826 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 222709292-Chloro-6-ethoxybenzonitrile収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d43f8b5cf77542039d4ba795f215839f
出典データセット
uspto-grants-2010_10
特許番号
US07812038B2

反応ノート

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