Ethane → 1-(4-Bromophenyl)Cyclopropanecarbonitrile

HRID 557888Notes

Reaction equation

HRID 557888 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[CH3:13][CH3:14]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6324EthaneHCID 14798Sodium HydroxideHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Sodium hydroxide (50% aqueous solution, 29.3 g, 0.505 mol) was added to a mixture of 4-bromo-benzeneacetonitrile (9.80 g, 0.0500 mol), benzyltriethylammonium chloride (0.90 g, 0.0040 mol), ethane, and 1-bromo-2-chloro-(14.5 g, 0.101 mol) at 50° C. overnight. The mixture was poured into ice-water (80 mL) and was extracted with ethyl ether (4×50 mL). The combined organic phase was washed with HCl aqueous solution (1N, 20 mL) and brine (2×30 mL) successively, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was the desired product, which was directly used in the next step without further purification.

Workup

  1. extractionwas extracted with ethyl ether (4×50 mL)
  2. washThe combined organic phase was washed with HCl aqueous solution (1N, 20 mL) and brine (2×30 mL) successively
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customwas directly used in the next step without further purification

Sources & evidence

ORD record
ord-d9a8705acf4a4063ad16998c705befb6
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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