1,3-Dibromopropane → 1-Phenylcyclobutanecarbonitrile

HRID 388822Notes

Reaction equation

HRID 388822 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15]Br.O.C1(C)C=CC=CC=1>CN(C=O)C>[C:3]1([C:9]2([C:10]#[N:11])[CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 22272177Toluene water

Product 1

HCID 844001-PhenylcyclobutanecarbonitrileYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (1.54 g, 64.1 mmol) dissolved in DMF (15 ml) and cooled to 0° C. Phenyl acetonitrile (3 g, 25.6 mmol) and 1,3-dibromopropane (5.2 g, 25.6 mmol) were dissolved in DMF (15 ml) and added to above mixture drop-wise at 0° C. This mixture was heated to rt and continued stirring for 2 h. Work up (H2O/Toluene) afforded the title compound (2.61 g) as crude, which was used in the next without further purification.

Workup

  1. additionadded to above mixture drop-wise at 0° C
  2. temperatureThis mixture was heated to rt

Sources & evidence

ORD record
ord-ab72727df51f4f6ca5969b20ac909818
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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