1,3-Dibromopropane → 1-(2-Bromo-4-fluorophenyl)cyclobutanecarbonitrile

HRID 558122Notes

Reaction equation

HRID 558122 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH2:11][C:12]#[N:13].Br[CH2:15][CH2:16][CH2:17]Br>C1(C)C=CC=CC=1.O>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1([C:12]#[N:13])[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 8263922-(2-Bromo-4-fluorophenyl)acetonitrile

Product 1

HCID 574450711-(2-Bromo-4-fluorophenyl)cyclobutanecarbonitrileYield 31.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Add potassium hydroxide (8.39 g, 150 mmol) and tetrabutylamine bromide (0.3 g, catalytic) to a solution of 2-(2-bromo-4-fluorophenyl)acetonitrile (4 g, 18.69 mmol) and 1,3-dibromopropane (4.15 g, 20.5 mmol) in toluene (20 mL). Stir it at 100° C. temperature for 2 h. Dilute the mixture with water and extract with ethyl acetate. Wash the organic layer with 1 N HCl and aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the crude product. Distill to give 1-(2-bromo-4-fluorophenyl)cyclobutanecarbonitrile (boiling point 110-120° C./0.3 Torr.) (1.5 g, 31%). MS (GC) m/z 253 [M]+.

Workup

  1. extractionextract with ethyl acetate
  2. washWash the organic layer with 1 N HCl and aqueous saturated sodium chloride
  3. dry with materialDry over magnesium sulfate
  4. customRemove the organic solvent
  5. customto give the crude product
  6. distillationDistill

Sources & evidence

ORD record
ord-7c60db5c0c5841d2bda6076f7ede6ea0
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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