1,3-Dibromopropane → 1-(2-Bromophenyl)cyclobutane-1-carbonitrile

HRID 1955261Notes

Reaction equation

HRID 1955261 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12].Br[CH2:14][CH2:15][CH2:16]Br.[H-]>CCCCC.CN(C=O)C.O>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1([C:11]#[N:12])[CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 296252-Bromobenzyl cyanideHCID 166653Hydride

Product 1

HCID 232949851-(2-Bromophenyl)cyclobutane-1-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolvent

Procedure

NaH (80% dispersion in mineral oil, 127 mmol) was washed several times with n-pentane and suspended in DMF (50 mL). A mixture of 2-bromophenylacetonitrile (51 mmol) and 1,3-dibromopropane (51 mmol) in DMF (50 mL) was added dropwise to the ice-cold mixture. The reaction mixture was stirred at room temperature for 3 h. Excess hydride was then decomposed by the cautious addition of H2O. Extraction with toluene, drying of the organic layer (MgSO4) and evaporation of the solvent afforded 1-(2-bromophenyl)-cyclobutanecarbonitrile that was refluxed with KOH (210 mmol) in ethyleneglycol (50 mL) for 4 h. The resulting solution was then allowed to cool to room temperature, toluene and H2O were added and the layers were separated. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to provide the desired product. The yield was 8.5 g (65%); 1H NMR (CDCl3) δ 1.80-1.93 (m, 1H), 2.20-2.40 (m, 1H), 2.54-2.65 (m, 2H), 2.86-2.96 (m, 2H), 7.07-7.15 (m, 1H), 7.29-7.37 (m, 2H), 7.53 (d, 1H)

Workup

  1. extractionExtraction with toluene
  2. dry with materialdrying of the organic layer (MgSO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-d58fc374977241669ba8383a257774d2
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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