(o-Chlorophenyl)acetonitrile → HCID 18934784, compound

HRID 1376021Notes

Reaction equation

HRID 1376021 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].[Br:11]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:11][CH:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[C:5]#[N:6]

Participants

6

Reactant 2

HCID 76112(o-Chlorophenyl)acetonitrileHCID 9834204N-Bromosuccinamide

Product 1

HCID 18934784HCID 18934784, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chlorobenzylcyanide (1.0 g, 6.60 mmol) in CCl4 (25 mL) was added N-bromosuccinamide (1.29 g, 7.26 mmol) and 2,2′-azobis-(2-methylpropionitrile) (0.05 g, 0.33 mmol). The reaction mixture was allowed to reflux for 48 h. The reaction mixture was then diluted with EtOAc (50 mL) and washed with 0.1 M NaOH (50 mL). The organic phase was concentrated to dryness yielding 1.0 g (66%) product.

Workup

  1. temperatureto reflux for 48 h
  2. washwashed with 0.1 M NaOH (50 mL)
  3. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-41980cd403e348529b6bf5199b2862b3
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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