N-bromobutanimide → 3-(5-Bromo-6-methoxy-2-methylpyridin-3-yl)benzonitrile

HRID 1921325Notes

Reaction equation

HRID 1921325 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:5][CH:4]=1.[Br:18]N1C(=O)CCC1=O>CO>[Br:18][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[C:7]([CH3:9])=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674923163-(6-Methoxy-2-methylpyridin-3-yl)benzonitrile

Product 1

HCID 674925473-(5-Bromo-6-methoxy-2-methylpyridin-3-yl)benzonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(6-methoxy-2-methylpyridin-3-yl)benzonitrile (3.00 g, 13.4 mmol), N-bromosuccinimide (2.89 g, 16.08 mmol) and methanol (150 mL) is stirred 66 hr at room temperature. The solids are collected by filtration to give 3-(5-bromo-6-methoxy-2-methylpyridin-3-yl)benzonitrile (1.20 g, 30%) as a white solid. LC/MS RT 4.19 min; MS m/e=303/305 (M); NMR (CDCl3) 7.65 (2H, m), 7.60 (1H, s), 7.56 (2H, m), 4.02 (3H, s), 2.37 (3H, s).

Workup

  1. filtrationThe solids are collected by filtration

Sources & evidence

ORD record
ord-1858840d328c4eda9bf964e18a98de44
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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