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

HRID 440535

Reaction equation

HRID 440535 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a510089955fd40b6a812525fcbad9149
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Linked notes

Loading…