N-bromobutanimide → HCID 86737889, compound

HRID 1278038Notes

Reaction equation

HRID 1278038 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][C:8]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[C:10]([O:11][CH3:12])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[CH:7]([C:8]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[C:10]([O:11][CH3:12])[CH:9]=1)[Br:19])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12362040HCID 12362040, compound

Product 1

HCID 86737889HCID 86737889, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat 58.2 g of homoveratric acid tert.-butyl ester and 43.3 g of N-bromosuccinimide under reflux for 2 hours in 1.3 liters of carbon tetrachloride under irradiation with a 500-watt immersion lamp. After cooling, filter out the succinimide and concentrate the filtrate. Dissolve the resulting concentrate in 250 ml of diethyl ether and extract the produced solution by shaking it with water. Free the ether solution from the solvent under a vacuum to obtain 50 g (66% of theory) of the title compound as a non-distillable oil.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter out the succinimide
  3. concentrationconcentrate the filtrate
  4. dissolutionDissolve the resulting
  5. concentrationconcentrate in 250 ml of diethyl ether
  6. extractionextract the produced solution

Sources & evidence

ORD record
ord-4669b90ea3854ce296503f0e875ce055
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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