Benzoyl Peroxide → HCID 59526058, compound

HRID 385899Notes

Reaction equation

HRID 385899 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 71720999Methyl (6-bromopyridin-2-yl)acetate

Product 1

HCID 59526058HCID 59526058, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl (6-bromopyridin-2-yl)acetate (Example 350, Step 1) (6.00 g, 26.1 mmol) in CCl4 (100 mL) were added NBS (4.87 g, 27.4 mmol) and benzoyl peroxide (474 mg, 1.96 mmol). The reaction was heated at reflux overnight. The solution was then cooled to room temperature, filtered, and evaporated. Silica gel chromatography (0-40% EtOAc/hexanes) afforded the title compound as a yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ebc3443d73534f84afa82345437fe0c9
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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