Acetonitrile → 7-(Bromomethyl)-2-naphthonitrile

HRID 1250317Notes

Reaction equation

HRID 1250317 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.C(#N)C.[CH3:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([C:27]#[N:28])=[CH:24]2)=[CH:19][CH:18]=1.[Br:29]N1C(=O)CCC1=O>C1(C)C=CC=CC=1.O>[Br:29][CH2:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([C:27]#[N:28])=[CH:24]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 98153237-Methyl-2-naphthalenecarbonitrile

Product 1

HCID 98377487-(Bromomethyl)-2-naphthonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2,2′-azobisisobutyronitrile (982 mg, 6 mmol) and acetonitrile (100 ml) were added to 7-methyl-2-naphthalene carbonitrile (10.0 g, 60 mmol) at room temperature. N-bromosuccinimide (10.6 g, 60 mmol) was added thereto, and the mixture was subjected to heating and refluxing for 2 hours. The resultant mixture was cooled to room temperature. Water (100 ml) and toluene (100 ml) were added to the mixture for extraction. The resultant organic layer was washed twice with water (100 ml). After concentration of a part of the organic layer under reduced pressure, analysis of the residue by reversed-phase chromatography by use of the obtained product from Example 11 as a standard sample revealed that 12.1 g of the title compound was obtained (82% yield).

Workup

  1. temperatureto heating
  2. temperaturerefluxing for 2 hours
  3. washThe resultant organic layer was washed twice with water (100 ml)
  4. customwas obtained (82% yield)

Sources & evidence

ORD record
ord-a01ce175cac741ae9e24b421ed528d39
Source dataset
uspto-grants-2002_01
Patent number
US06337405B1

Reaction notes

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