1,3-Dibromopropane → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 223464

Reaction equation

HRID 223464 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16]Br>CS(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2([C:7]#[N:8])[CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileYield 85.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

4-Chlorobenzyl cyanide (10 g) in dry DMSO (20 ml) was added over 5 min to a stirred suspension of sodium hydride (4.4 g) in DMSO at 25° C. under argon. The mixture was stirred for 30 minutes then a solution of 1,3-dibromopropane (27 g) in dry DMSO (50 ml) was added over 30 minutes while maintaining the temperature of the reaction mixture at 25°-30° C. After stirring an additional 40 minutes at this temperature the reaction mixture was added to ice water (500 ml) and extracted with dichloromethane (3×75 ml). The extracts were evaporated and the residue extracted with diethyl ether (4×50 ml). The ether extracts were washed with water, dried over anhydrous sodium sulphate and evaporated to yield an oil (10.8 g) which on distillation gave the nitrile [bp 90°/10-6Torr.] yield 5.4 g (43%).

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at 25°-30° C
  2. stirringAfter stirring an additional 40 minutes at this temperature the reaction mixture
  3. extractionextracted with dichloromethane (3×75 ml)
  4. customThe extracts were evaporated
  5. extractionthe residue extracted with diethyl ether (4×50 ml)
  6. washThe ether extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-be96759ba097479885748c985dc5144a
Source dataset
uspto-grants-1982_10
Patent number
US04355042

Linked notes

Loading…