Azobisisobutyronitrile → 7-(Bromomethyl)-2-naphthonitrile

HRID 1069542Notes

Reaction equation

N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([C:24]#[N:25])=[CH:21]2)=[CH:16][CH:15]=1.[Br:26]N1C(=O)CCC1=O>>[Br:26][CH2:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([C:24]#[N:25])=[CH:21]2)=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 6547Azobisisobutyronitrile

HCID 67184N-bromobutanimide

HCID 98153237-Methyl-2-naphthalenecarbonitrile

Product 1

HCID 98377487-(Bromomethyl)-2-naphthonitrileYield 74%

Conditions

Temperature: 80 °C

Procedure

2,2′-azobisisobutyronitrile (491 mg, 3 mmol) and normalbutyronitrile (50 ml) were added to 7-methyl-2-naphthalene carbonitrile (5.0 g, 30 mmol) at room temperature. N-bromosuccinimide (5.3 g, 30 mmol) was added thereto, and the mixture was heated at an internal temperature of 80° C. for 2 hours. After that, the experiment was conducted in the same way as Example 12. Analysis by reversed-phase chromatography by use of the obtained product from Example 11 as a standard sample revealed that 5.4 g of the title compound was obtained (74% yield).

Sources & evidence

ORD record: ord-ee85342ffafc4b9194a04fc401ce6647
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06252088B1

Reaction notes

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