4-Bromobutyronitrile → 5-benzyl-3,4-dihydro-2H-pyrrole

HRID 1045700

Reaction equation

HRID 1045700 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[CH2:7]([Mg]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.C(OCC)C>[CH2:7]([C:2]1[CH2:3][CH2:4][CH2:5][N:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 214124-BromobutyronitrileHCID 178419663HCID 178419663, compound

Product 1

HCID 2240185-benzyl-3,4-dihydro-2H-pyrroleYield 132.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-bromobutyronitrile (2.0 g, 13.5 mmol) in toluene (70 ml) was added 1.0 M benzylmagnesium bromide (20.0 ml, 20.0 mmol) in diethyl ether (70 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was partitioned between 0.1N hydrochloric acid and ethyl acetate, and the organic layer was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford 5-benzyl-3,4-dihydro-2H-pyrrole (2.85 g). This compound was used without further purification.

Workup

  1. customThe mixture was partitioned between 0.1N hydrochloric acid and ethyl acetate
  2. washthe organic layer was washed with aqueous sodium hydrogen carbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ed19ab4a3214edb8f98f66172edcdf8
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Linked notes

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