Acetonitrile → 7-(Bromomethyl)-2-naphthonitrile

HRID 1058160Notes

Reaction equation

HRID 1058160 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 78%

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 the organic layer under reduced pressure, the residue was subjected to silica-gel-column chromatography to yield 11.4 g of the title compound (78% yield). The data measured by instruments agreed with the data described in J. Med. Chem., 1991, 3105.

Workup

  1. temperatureto heating
  2. temperaturerefluxing for 2 hours
  3. washThe resultant organic layer was washed twice with water (100 ml)

Sources & evidence

ORD record
ord-9c27a4095d234721a14d82df3523334f
Source dataset
uspto-grants-2003_02
Patent number
US06515142B2

Reaction notes

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