Benzoyl Peroxide → HCID 18432923, compound

HRID 2305434Notes

Reaction equation

HRID 2305434 reaction equation
[N+:1]([C:4]1[C:9]([Br:10])=[C:8]([CH3:11])[C:7]([Br:12])=[CH:6][N:5]=1)([O-:3])=[O:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:31]NC(=O)CCC(N)=O>C1C=CC=CC=1>[N+:1]([C:4]1[C:9]([Br:10])=[C:8]([CH2:11][Br:31])[C:7]([Br:12])=[CH:6][N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 184329202-Nitro-3,5-dibromo-4-methylpyridine

Product 1

HCID 18432923HCID 18432923, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-nitro-3,5-dibromo-4-methylpyridine(10.7 g, 36.15 mmol) in benzene(20 ml) was added benzoyl peroxide(1.0 g, 5.42 mmol) and N-bromosuccinamide(7.75 g, 42.18 mmol). The mixture was stirred at 110° C. and irradiated with a 150-W floodlight for 48 hrs. The solvent was evaporated and chromatography of the resulting solid on silica gel (10%EtOAc/Hexane) gave the desired product(4.5 g, 33%). 1H NMR (CDCl3): δ 8.56 (s, 1H), 4.76 (s, 2H).

Workup

  1. customirradiated with a 150-W floodlight for 48 hrs
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bdef4635e924443db51aff94b6ce735b
Source dataset
uspto-grants-2002_08
Patent number
US06440993B1

Reaction notes

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