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

HRID 440535

반응식

HRID 440535 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a510089955fd40b6a812525fcbad9149
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519034

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