N-bromobutanimide → HCID 45117088, compound

HRID 2388147Notes

Reaction equation

HRID 2388147 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH2:11][Br:18])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70838Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate

Product 1

HCID 45117088HCID 45117088, compoundYield 102,372%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid ethyl ester (5.02 g, 0.02 mol), N-bromosuccinimide (4.06 g, 0.02 mmol) and benzoyl peroxide (263 mg, 1.09 mmol) in carbon tetrachloride (80 ml) was refluxed for 20 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound as a yellow oil (6.35 g) that was used in the following step without further purification: 1H NMR (CDCl3, 200 MHz): δ=7.61 (m, 2H), 7.43 (m, 3H), 4.80 (s, 2H), 4.25 (q, J=7.0 Hz, 2H), 1.26 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturewas refluxed for 20 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine before it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6db46bf246264ba4918a117270591212
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…