N-bromobutanimide → HCID 11043787, compound

HRID 322022Notes

Reaction equation

HRID 322022 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11].C1C(=O)N([Br:22])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10171305HCID 10171305, compound

Product 1

HCID 11043787HCID 11043787, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of ethyl(E)-3-(2-methylphenyl)-2-propenoate (20.0 g; 105 mmol) and NBS (19.64 g; 110.3 mmol) in refluxing CCl4 was added benzoyl peroxide (1.27 g) and the mixture was stirred for 12 h. The solution was cooled to r.t., filtered and concentrated. Flash chromatography with EtOAc:hexane 5:95 yielded the title compound (14.18 g, 50%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e124b1dda3464fffab00c156a54b6c75
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

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