Benzoyl Peroxide → 5-(Bromomethyl)-2-[(4-nitrophenyl)sulfanyl]pyridine-3-carbonitrile
Reaction equation
[C:1]([C:3]1[C:4]([S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1)#[N:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[C:1]([C:3]1[C:4]([S:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:5][CH:6]=[C:7]([CH2:9][Br:20])[CH:8]=1)#[N:2]Participants
5
Procedure
A mixture of 60.00 g (0.221 mol) of 3-cyano-2-(4-nitrophenylthio)-5-methylpyridine, 39.37 g (0.221 mol) of N-bromosuccinimide, 3.0 g of benzoyl peroxide and 60 mL of benzene was refluxed for 16 hours while being irradiated with a 275-W sunlamp. The solvent was removed under reduced pressure and the residue was shaken with a mixture of 1 L of water and 1 L of methylene chloride. The organic layer was separated, washed with 1 L of water, dried over anhydrous magnesium sulfate, and filtered. Removal of the solvent by evaporation under reduced pressure yielded 3-cyano-2-(4-nitrophenylthio)-5-bromomethylpyridine which can be used in the following step without further purification.
Workup
- temperaturewas refluxed for 16 hours
- customwhile being irradiated with a 275-W sunlamp
- customThe solvent was removed under reduced pressure
- customThe organic layer was separated
- washwashed with 1 L of water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customRemoval of the solvent
- customby evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-21b027930e4e4e02ae9de412f59b679b
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04684653
Reaction notes
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