N-bromobutanimide → HCID 59299491, compound

HRID 1013802Notes

Reaction equation

HRID 1013802 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH3:9])[C:3]=1[Cl:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][Br:11])[C:3]=1[Cl:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 148011751-Bromo-2,4-dichloro-3-methylbenzene

Product 1

HCID 59299491HCID 59299491, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

Treat a mixture of 1-bromo-2,4-dichloro-3-methyl-benzene (76.01 g, 0.316 mol) and N-bromosuccinimide (59.2 g, 0.332 mol) in CCl4 (500 mL) with benzoyl peroxide (0.77 g, 3.18 mmol) and is heat to reflux for 6 hours under N2. Cool the reaction mixture to 0° C. and filter using hexanes to rinse the solids. Extract the filtrate with water and saturated NaHCO3. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford 97.89 g (97%) of the titled product. Rf=0.34 (100% hexanes).

Workup

  1. additionTreat
  2. temperatureis heat
  3. temperatureto reflux for 6 hours under N2
  4. filtrationfilter
  5. washto rinse the solids
  6. extractionExtract the filtrate with water and saturated NaHCO3
  7. dry with materialDry the organic layer (Na2SO4)
  8. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-35f8228324a449c0ae534574be6b9923
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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