1,2-Dibromoethane → 1-Phenylcyclopropanecarbonitrile

HRID 845113Notes

Reaction equation

HRID 845113 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14]Br>CS(C)=O>[C:1]1([C:7]2([C:8]#[N:9])[CH2:14][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 702881-PhenylcyclopropanecarbonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

Phenylacetonitrile (5.85 g, 50 mmol) in DMSO (dimethylsulfoxide) (20 mL) is added dropwise over 45 min to a slurry of oil-free NaH (3.0 g, 125 mmol) in stirred DMSO (100 mL) at 25° under N2. Vigorous gas evolution occurs. After a further 30 min 1,2-dibromoethane (14.1 g, 75 mmol) in DMSO (20 mL) is added dropwise over 1 h. The reaction mixture turns purple, heats up to about 50°, and further gas evolution occurs. After a further 1 h the reaction mixture is poured slowly onto ice water (250 mL, gas evolution), and is extracted with ether (3×50 mL). The combined extracts are washed with water (2×100 mL) and saturated brine (100 mL) and dried (MgSO4). The solvent is removed under reduced pressure to give 1-phenylcyclopropane carbonitrile (6.58 g, 92%) as a mobile brown oil. Nmr δ (CDCl3) 7.25-7.40 (5H, m), 1.6-1.8, 1.2-1.45 (2H and 2H, AA'BB').

Workup

  1. customheats up to about 50°
  2. additionAfter a further 1 h the reaction mixture is poured slowly onto ice water (250 mL, gas evolution)
  3. extractionis extracted with ether (3×50 mL)
  4. washThe combined extracts are washed with water (2×100 mL) and saturated brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-43bf6615d4e3485bb89d0531779f9d00
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

Loading…