Water → 1-[4-(Trifluoromethoxy)phenyl]cyclobutanecarbonitrile

HRID 440535

反応式

HRID 440535 の反応式
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][CH2:18]Br.[H-].[Na+].O>O1CCCC1.CN(C)C=O>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]#[N:12])[CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 1426764-(Trifluoromethoxy)phenylacetonitrile

生成物 1

HCID 219020771-[4-(Trifluoromethoxy)phenyl]cyclobutanecarbonitrile収率 66.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
20 °C

実験手順

A solution of 4-trifluoromethoxyphenylacetonitrile (38.9 g) and 1,3-dibromopropane (39.1 g) in tetrahydrofuran (50 ml) was added under argon to a stirred solution of 50% sodium hydride (19.2 g) in tetrahydrofuran (200 ml) and dimethylformamide (25 ml) at 25°-30° C. over 1 hour. The mixture was stirred at 20° C. for 1.5 hours, then at 30°-40° C. for 1 hour, then cooled and water added. The mixture was filtered and washed with ether. The organic layer was washed with water, dried over magnesium sulphate and the solvent removed by evaporation. The residue was distilled (b.p. 111°-117° C./10 mbar) to give 1-(4-trifluoromethoxyphenyl)cyclobutanecarbonitrile (30.98 g).

後処理

  1. waitat 30°-40° C. for 1 hour
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. washwashed with ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed by evaporation
  8. distillationThe residue was distilled (b.p. 111°-117° C./10 mbar)

出典と根拠

ORDレコード
ord-a510089955fd40b6a812525fcbad9149
出典データセット
uspto-grants-1996_05
特許番号
US05519034

関連ノート

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