Benzoyl Peroxide → HCID 19902825, compound

HRID 2372180Notes

Reaction equation

HRID 2372180 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([CH2:13][CH3:14])[N:3]=1.[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([CH:13]([Br:15])[CH3:14])[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19902815HCID 19902815, compound

Product 1

HCID 19902825HCID 19902825, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl 6-chloro-2-ethylnicotinate (1.0 g, 4.7 mmol), N-bromosuccinimide (0.85 g, 4.8 mmol) and benzoyl peroxide (10 mg) in 10 ml of carbon tetrachloride is heated to reflux while irradiated with a floodlamp for 3 hours. The reaction mixture is cooled and the solid succinimide is removed by filtration. The solid is washed several times with carbon tetrachloride and the filtrate is stripped by rotoevaporation to give ethyl 6-chloro-2-(1-bromoethyl)nicotinate.

Workup

  1. temperatureto reflux
  2. customwhile irradiated with a floodlamp for 3 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe solid succinimide is removed by filtration
  5. washThe solid is washed several times with carbon tetrachloride

Sources & evidence

ORD record
ord-98da79a596a64e05b3a8bd29bc114c3f
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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