Benzoyl Peroxide → 6-[4-(Bromomethyl)phenyl]-2-chloro-5-phenylnicotinonitrile

HRID 1869273Notes

Reaction equation

HRID 1869273 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:30])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:30][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[N:9]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 211031982-Chloro-6-(4-methylphenyl)-5-phenylnicotinonitrile

Product 1

HCID 866076536-[4-(Bromomethyl)phenyl]-2-chloro-5-phenylnicotinonitrile

Procedure

The solution of 2-chloro-6-(4-methylphenyl)-5-phenylnicotinonitrile (1-4; 0.066 g, 0.217 mmol), NBS (0.046 g, 0.26 mmol) and benzoylperoxide (0.010 g, 0.043 mmol) in CDCl3 (2 mL) was heated to reflux overnight. The mixture was concentrated to give 6-[4-(bromomethyl)phenyl]-2-chloro-5-phenylnicotinonitrile (1-5) and used without further purification. LRMS m/z (M+H) Calcd: 383.7, found: 383.1.

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-bcd55818470148cfba8b16b7b3edc605
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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